feat(mattermost): configurable mention behavior — respond without @mention

Adds MATTERMOST_REQUIRE_MENTION and MATTERMOST_FREE_RESPONSE_CHANNELS env vars, matching Discord's existing mention gating pattern. - MATTERMOST_REQUIRE_MENTION=false: respond to all channel messages - MATTERMOST_FREE_RESPONSE_CHANNELS=id1,id2: specific channels where bot responds without @mention even when require_mention is true - DMs always respond regardless of mention settings - @mention is now stripped from message text (clean agent input) 7 new tests for mention gating, free-response channels, DM bypass, and mention stripping. Updated existing test for mention stripping. Docs: updated mattermost.md with Mention Behavior section, environment-variables.md with new vars, config.py with metadata.
fix(tools): use non-deprecated streamable_http_client for MCP HTTP transport (#3646 )
2026-03-28 21:10:24 -07:00 · 2026-03-28 18:20:49 -07:00 · 2026-03-28 17:52:32 -07:00 · 2026-03-28 17:49:56 -07:00 · 2026-03-28 17:35:53 -07:00 · 2026-03-28 17:29:37 -07:00
176 changed files with 11948 additions and 1239 deletions
@@ -59,12 +59,25 @@ OPENCODE_ZEN_API_KEY=
 # OpenCode Go provides access to open models (GLM-5, Kimi K2.5, MiniMax M2.5)
 # $10/month subscription. Get your key at: https://opencode.ai/auth
 OPENCODE_GO_API_KEY=
+
+# =============================================================================
+# LLM PROVIDER (Hugging Face Inference Providers)
+# =============================================================================
+# Hugging Face routes to 20+ open models via unified OpenAI-compatible endpoint.
+# Free tier included ($0.10/month), no markup on provider rates.
+# Get your token at: https://huggingface.co/settings/tokens
+# Required permission: "Make calls to Inference Providers"
+HF_TOKEN=
 # OPENCODE_GO_BASE_URL=https://opencode.ai/zen/go/v1  # Override default base URL

 # =============================================================================
 # TOOL API KEYS
 # =============================================================================

+# Exa API Key - AI-native web search and contents
+# Get at: https://exa.ai
+EXA_API_KEY=
+
 # Parallel API Key - AI-native web search and extract
 # Get at: https://parallel.ai
 PARALLEL_API_KEY=
@@ -0,0 +1,348 @@
+# Hermes Agent v0.5.0 (v2026.3.28)
+
+**Release Date:** March 28, 2026
+
+> The hardening release — Hugging Face provider, /model command overhaul, Telegram Private Chat Topics, native Modal SDK, plugin lifecycle hooks, tool-use enforcement for GPT models, Nix flake, 50+ security and reliability fixes, and a comprehensive supply chain audit.
+
+---
+
+## ✨ Highlights
+
+- **Nous Portal now supports 400+ models** — The Nous Research inference portal has expanded dramatically, giving Hermes Agent users access to over 400 models through a single provider endpoint
+
+- **Hugging Face as a first-class inference provider** — Full integration with HF Inference API including curated agentic model picker that maps to OpenRouter analogues, live `/models` endpoint probe, and setup wizard flow ([#3419](https://github.com/NousResearch/hermes-agent/pull/3419), [#3440](https://github.com/NousResearch/hermes-agent/pull/3440))
+
+- **Telegram Private Chat Topics** — Project-based conversations with functional skill binding per topic, enabling isolated workflows within a single Telegram chat ([#3163](https://github.com/NousResearch/hermes-agent/pull/3163))
+
+- **Native Modal SDK backend** — Replaced swe-rex dependency with native Modal SDK (`Sandbox.create.aio` + `exec.aio`), eliminating tunnels and simplifying the Modal terminal backend ([#3538](https://github.com/NousResearch/hermes-agent/pull/3538))
+
+- **Plugin lifecycle hooks activated** — `pre_llm_call`, `post_llm_call`, `on_session_start`, and `on_session_end` hooks now fire in the agent loop and CLI/gateway, completing the plugin hook system ([#3542](https://github.com/NousResearch/hermes-agent/pull/3542))
+
+- **Improved OpenAI Model Reliability** — Added `GPT_TOOL_USE_GUIDANCE` to prevent GPT models from describing intended actions instead of making tool calls, plus automatic stripping of stale budget warnings from conversation history that caused models to avoid tools across turns ([#3528](https://github.com/NousResearch/hermes-agent/pull/3528))
+
+- **Nix flake** — Full uv2nix build, NixOS module with persistent container mode, auto-generated config keys from Python source, and suffix PATHs for agent-friendliness ([#20](https://github.com/NousResearch/hermes-agent/pull/20), [#3274](https://github.com/NousResearch/hermes-agent/pull/3274), [#3061](https://github.com/NousResearch/hermes-agent/pull/3061)) by @alt-glitch
+
+- **Supply chain hardening** — Removed compromised `litellm` dependency, pinned all dependency version ranges, regenerated `uv.lock` with hashes, added CI workflow scanning PRs for supply chain attack patterns, and bumped deps to fix CVEs ([#2796](https://github.com/NousResearch/hermes-agent/pull/2796), [#2810](https://github.com/NousResearch/hermes-agent/pull/2810), [#2812](https://github.com/NousResearch/hermes-agent/pull/2812), [#2816](https://github.com/NousResearch/hermes-agent/pull/2816), [#3073](https://github.com/NousResearch/hermes-agent/pull/3073))
+
+- **Anthropic output limits fix** — Replaced hardcoded 16K `max_tokens` with per-model native output limits (128K for Opus 4.6, 64K for Sonnet 4.6), fixing "Response truncated" and thinking-budget exhaustion on direct Anthropic API ([#3426](https://github.com/NousResearch/hermes-agent/pull/3426), [#3444](https://github.com/NousResearch/hermes-agent/pull/3444))
+
+---
+
+## 🏗️ Core Agent & Architecture
+
+### New Provider: Hugging Face
+- First-class Hugging Face Inference API integration with auth, setup wizard, and model picker ([#3419](https://github.com/NousResearch/hermes-agent/pull/3419))
+- Curated model list mapping OpenRouter agentic defaults to HF equivalents — providers with 8+ curated models skip live `/models` probe for speed ([#3440](https://github.com/NousResearch/hermes-agent/pull/3440))
+- Added glm-5-turbo to Z.AI provider model list ([#3095](https://github.com/NousResearch/hermes-agent/pull/3095))
+
+### Provider & Model Improvements
+- `/model` command overhaul — extracted shared `switch_model()` pipeline for CLI and gateway, custom endpoint support, provider-aware routing ([#2795](https://github.com/NousResearch/hermes-agent/pull/2795), [#2799](https://github.com/NousResearch/hermes-agent/pull/2799))
+- Removed `/model` slash command from CLI and gateway in favor of `hermes model` subcommand ([#3080](https://github.com/NousResearch/hermes-agent/pull/3080))
+- Preserve `custom` provider instead of silently remapping to `openrouter` ([#2792](https://github.com/NousResearch/hermes-agent/pull/2792))
+- Read root-level `provider` and `base_url` from config.yaml into model config ([#3112](https://github.com/NousResearch/hermes-agent/pull/3112))
+- Align Nous Portal model slugs with OpenRouter naming ([#3253](https://github.com/NousResearch/hermes-agent/pull/3253))
+- Fix Alibaba provider default endpoint and model list ([#3484](https://github.com/NousResearch/hermes-agent/pull/3484))
+- Allow MiniMax users to override `/v1` → `/anthropic` auto-correction ([#3553](https://github.com/NousResearch/hermes-agent/pull/3553))
+- Migrate OAuth token refresh to `platform.claude.com` with fallback ([#3246](https://github.com/NousResearch/hermes-agent/pull/3246))
+
+### Agent Loop & Conversation
+- **Improved OpenAI model reliability** — `GPT_TOOL_USE_GUIDANCE` prevents GPT models from describing actions instead of calling tools + automatic budget warning stripping from history ([#3528](https://github.com/NousResearch/hermes-agent/pull/3528))
+- **Surface lifecycle events** — All retry, fallback, and compression events now surface to the user as formatted messages ([#3153](https://github.com/NousResearch/hermes-agent/pull/3153))
+- **Anthropic output limits** — Per-model native output limits instead of hardcoded 16K `max_tokens` ([#3426](https://github.com/NousResearch/hermes-agent/pull/3426))
+- **Thinking-budget exhaustion detection** — Skip useless continuation retries when model uses all output tokens on reasoning ([#3444](https://github.com/NousResearch/hermes-agent/pull/3444))
+- Always prefer streaming for API calls to prevent hung subagents ([#3120](https://github.com/NousResearch/hermes-agent/pull/3120))
+- Restore safe non-streaming fallback after stream failures ([#3020](https://github.com/NousResearch/hermes-agent/pull/3020))
+- Give subagents independent iteration budgets ([#3004](https://github.com/NousResearch/hermes-agent/pull/3004))
+- Update `api_key` in `_try_activate_fallback` for subagent auth ([#3103](https://github.com/NousResearch/hermes-agent/pull/3103))
+- Graceful return on max retries instead of crashing thread ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Count compression restarts toward retry limit ([#3070](https://github.com/NousResearch/hermes-agent/pull/3070))
+- Include tool tokens in preflight estimate, guard context probe persistence ([#3164](https://github.com/NousResearch/hermes-agent/pull/3164))
+- Update context compressor limits after fallback activation ([#3305](https://github.com/NousResearch/hermes-agent/pull/3305))
+- Validate empty user messages to prevent Anthropic API 400 errors ([#3322](https://github.com/NousResearch/hermes-agent/pull/3322))
+- GLM reasoning-only and max-length handling ([#3010](https://github.com/NousResearch/hermes-agent/pull/3010))
+- Increase API timeout default from 900s to 1800s for slow-thinking models ([#3431](https://github.com/NousResearch/hermes-agent/pull/3431))
+- Send `max_tokens` for Claude/OpenRouter + retry SSE connection errors ([#3497](https://github.com/NousResearch/hermes-agent/pull/3497))
+- Prevent AsyncOpenAI/httpx cross-loop deadlock in gateway mode ([#2701](https://github.com/NousResearch/hermes-agent/pull/2701)) by @ctlst
+
+### Streaming & Reasoning
+- **Persist reasoning across gateway session turns** with new schema v6 columns (`reasoning`, `reasoning_details`, `codex_reasoning_items`) ([#2974](https://github.com/NousResearch/hermes-agent/pull/2974))
+- Detect and kill stale SSE connections ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Fix stale stream detector race causing spurious `RemoteProtocolError` ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Skip duplicate callback for `<think>`-extracted reasoning during streaming ([#3116](https://github.com/NousResearch/hermes-agent/pull/3116))
+- Preserve reasoning fields in `rewrite_transcript` ([#3311](https://github.com/NousResearch/hermes-agent/pull/3311))
+- Preserve Gemini thought signatures in streamed tool calls ([#2997](https://github.com/NousResearch/hermes-agent/pull/2997))
+- Ensure first delta is fired during reasoning updates ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+### Session & Memory
+- **Session search recent sessions mode** — Omit query to browse recent sessions with titles, previews, and timestamps ([#2533](https://github.com/NousResearch/hermes-agent/pull/2533))
+- **Session config surfacing** on `/new`, `/reset`, and auto-reset ([#3321](https://github.com/NousResearch/hermes-agent/pull/3321))
+- **Third-party session isolation** — `--source` flag for isolating sessions by origin ([#3255](https://github.com/NousResearch/hermes-agent/pull/3255))
+- Add `/resume` CLI handler, session log truncation guard, `reopen_session` API ([#3315](https://github.com/NousResearch/hermes-agent/pull/3315))
+- Clear compressor summary and turn counter on `/clear` and `/new` ([#3102](https://github.com/NousResearch/hermes-agent/pull/3102))
+- Surface silent SessionDB failures that cause session data loss ([#2999](https://github.com/NousResearch/hermes-agent/pull/2999))
+- Session search fallback preview on summarization failure ([#3478](https://github.com/NousResearch/hermes-agent/pull/3478))
+- Prevent stale memory overwrites by flush agent ([#2687](https://github.com/NousResearch/hermes-agent/pull/2687))
+
+### Context Compression
+- Replace dead `summary_target_tokens` with ratio-based scaling ([#2554](https://github.com/NousResearch/hermes-agent/pull/2554))
+- Expose `compression.target_ratio`, `protect_last_n`, and `threshold` in `DEFAULT_CONFIG` ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Restore sane defaults and cap summary at 12K tokens ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Preserve transcript on `/compress` and hygiene compression ([#3556](https://github.com/NousResearch/hermes-agent/pull/3556))
+- Update context pressure warnings and token estimates after compaction ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+### Architecture & Dependencies
+- **Remove mini-swe-agent dependency** — Inline Docker and Modal backends directly ([#2804](https://github.com/NousResearch/hermes-agent/pull/2804))
+- **Replace swe-rex with native Modal SDK** for Modal backend ([#3538](https://github.com/NousResearch/hermes-agent/pull/3538))
+- **Plugin lifecycle hooks** — `pre_llm_call`, `post_llm_call`, `on_session_start`, `on_session_end` now fire in the agent loop ([#3542](https://github.com/NousResearch/hermes-agent/pull/3542))
+- Fix plugin toolsets invisible in `hermes tools` and standalone processes ([#3457](https://github.com/NousResearch/hermes-agent/pull/3457))
+- Consolidate `get_hermes_home()` and `parse_reasoning_effort()` ([#3062](https://github.com/NousResearch/hermes-agent/pull/3062))
+- Remove unused Hermes-native PKCE OAuth flow ([#3107](https://github.com/NousResearch/hermes-agent/pull/3107))
+- Remove ~100 unused imports across 55 files ([#3016](https://github.com/NousResearch/hermes-agent/pull/3016))
+- Fix 154 f-strings, simplify getattr/URL patterns, remove dead code ([#3119](https://github.com/NousResearch/hermes-agent/pull/3119))
+
+---
+
+## 📱 Messaging Platforms (Gateway)
+
+### Telegram
+- **Private Chat Topics** — Project-based conversations with functional skill binding per topic, enabling isolated workflows within a single Telegram chat ([#3163](https://github.com/NousResearch/hermes-agent/pull/3163))
+- **Auto-discover fallback IPs via DNS-over-HTTPS** when `api.telegram.org` is unreachable ([#3376](https://github.com/NousResearch/hermes-agent/pull/3376))
+- **Configurable reply threading mode** ([#2907](https://github.com/NousResearch/hermes-agent/pull/2907))
+- Fall back to no `thread_id` on "Message thread not found" BadRequest ([#3390](https://github.com/NousResearch/hermes-agent/pull/3390))
+- Self-reschedule reconnect when `start_polling` fails after 502 ([#3268](https://github.com/NousResearch/hermes-agent/pull/3268))
+
+### Discord
+- Stop phantom typing indicator after agent turn completes ([#3003](https://github.com/NousResearch/hermes-agent/pull/3003))
+
+### Slack
+- Send tool call progress messages to correct Slack thread ([#3063](https://github.com/NousResearch/hermes-agent/pull/3063))
+- Scope progress thread fallback to Slack only ([#3488](https://github.com/NousResearch/hermes-agent/pull/3488))
+
+### WhatsApp
+- Download documents, audio, and video media from messages ([#2978](https://github.com/NousResearch/hermes-agent/pull/2978))
+
+### Matrix
+- Add missing Matrix entry in `PLATFORMS` dict ([#3473](https://github.com/NousResearch/hermes-agent/pull/3473))
+- Harden e2ee access-token handling ([#3562](https://github.com/NousResearch/hermes-agent/pull/3562))
+- Add backoff for `SyncError` in sync loop ([#3280](https://github.com/NousResearch/hermes-agent/pull/3280))
+
+### Signal
+- Track SSE keepalive comments as connection activity ([#3316](https://github.com/NousResearch/hermes-agent/pull/3316))
+
+### Email
+- Prevent unbounded growth of `_seen_uids` in EmailAdapter ([#3490](https://github.com/NousResearch/hermes-agent/pull/3490))
+
+### Gateway Core
+- **Config-gated `/verbose` command** for messaging platforms — toggle tool output verbosity from chat ([#3262](https://github.com/NousResearch/hermes-agent/pull/3262))
+- **Background review notifications** delivered to user chat ([#3293](https://github.com/NousResearch/hermes-agent/pull/3293))
+- **Retry transient send failures** and notify user on exhaustion ([#3288](https://github.com/NousResearch/hermes-agent/pull/3288))
+- Recover from hung agents — `/stop` hard-kills session lock ([#3104](https://github.com/NousResearch/hermes-agent/pull/3104))
+- Thread-safe `SessionStore` — protect `_entries` with `threading.Lock` ([#3052](https://github.com/NousResearch/hermes-agent/pull/3052))
+- Fix gateway token double-counting with cached agents — use absolute set instead of increment ([#3306](https://github.com/NousResearch/hermes-agent/pull/3306), [#3317](https://github.com/NousResearch/hermes-agent/pull/3317))
+- Fingerprint full auth token in agent cache signature ([#3247](https://github.com/NousResearch/hermes-agent/pull/3247))
+- Silence background agent terminal output ([#3297](https://github.com/NousResearch/hermes-agent/pull/3297))
+- Include per-platform `ALLOW_ALL` and `SIGNAL_GROUP` in startup allowlist check ([#3313](https://github.com/NousResearch/hermes-agent/pull/3313))
+- Include user-local bin paths in systemd unit PATH ([#3527](https://github.com/NousResearch/hermes-agent/pull/3527))
+- Track background task references in `GatewayRunner` ([#3254](https://github.com/NousResearch/hermes-agent/pull/3254))
+- Add request timeouts to HA, Email, Mattermost, SMS adapters ([#3258](https://github.com/NousResearch/hermes-agent/pull/3258))
+- Add media download retry to Mattermost, Slack, and base cache ([#3323](https://github.com/NousResearch/hermes-agent/pull/3323))
+- Detect virtualenv path instead of hardcoding `venv/` ([#2797](https://github.com/NousResearch/hermes-agent/pull/2797))
+- Use `TERMINAL_CWD` for context file discovery, not process cwd ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Stop loading hermes repo AGENTS.md into gateway sessions (~10k wasted tokens) ([#2891](https://github.com/NousResearch/hermes-agent/pull/2891))
+
+---
+
+## 🖥️ CLI & User Experience
+
+### Interactive CLI
+- **Configurable busy input mode** + fix `/queue` always working ([#3298](https://github.com/NousResearch/hermes-agent/pull/3298))
+- **Preserve user input on multiline paste** ([#3065](https://github.com/NousResearch/hermes-agent/pull/3065))
+- **Tool generation callback** — streaming "preparing terminal…" updates during tool argument generation ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Show tool progress for substantive tools, not just "preparing" ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Buffer reasoning preview chunks and fix duplicate display ([#3013](https://github.com/NousResearch/hermes-agent/pull/3013))
+- Prevent reasoning box from rendering 3x during tool-calling loops ([#3405](https://github.com/NousResearch/hermes-agent/pull/3405))
+- Eliminate "Event loop is closed" / "Press ENTER to continue" during idle — three-layer fix with `neuter_async_httpx_del()`, custom exception handler, and stale client cleanup ([#3398](https://github.com/NousResearch/hermes-agent/pull/3398))
+- Fix status bar shows 26K instead of 260K for token counts with trailing zeros ([#3024](https://github.com/NousResearch/hermes-agent/pull/3024))
+- Fix status bar duplicates and degrades during long sessions ([#3291](https://github.com/NousResearch/hermes-agent/pull/3291))
+- Refresh TUI before background task output to prevent status bar overlap ([#3048](https://github.com/NousResearch/hermes-agent/pull/3048))
+- Suppress KawaiiSpinner animation under `patch_stdout` ([#2994](https://github.com/NousResearch/hermes-agent/pull/2994))
+- Skip KawaiiSpinner when TUI handles tool progress ([#2973](https://github.com/NousResearch/hermes-agent/pull/2973))
+- Guard `isatty()` against closed streams via `_is_tty` property ([#3056](https://github.com/NousResearch/hermes-agent/pull/3056))
+- Ensure single closure of streaming boxes during tool generation ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Cap context pressure percentage at 100% in display ([#3480](https://github.com/NousResearch/hermes-agent/pull/3480))
+- Clean up HTML error messages in CLI display ([#3069](https://github.com/NousResearch/hermes-agent/pull/3069))
+- Show HTTP status code and 400 body in API error output ([#3096](https://github.com/NousResearch/hermes-agent/pull/3096))
+- Extract useful info from HTML error pages, dump debug on max retries ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Prevent TypeError on startup when `base_url` is None ([#3068](https://github.com/NousResearch/hermes-agent/pull/3068))
+- Prevent update crash in non-TTY environments ([#3094](https://github.com/NousResearch/hermes-agent/pull/3094))
+- Handle EOFError in sessions delete/prune confirmation prompts ([#3101](https://github.com/NousResearch/hermes-agent/pull/3101))
+- Catch KeyboardInterrupt during `flush_memories` on exit and in exit cleanup handlers ([#3025](https://github.com/NousResearch/hermes-agent/pull/3025), [#3257](https://github.com/NousResearch/hermes-agent/pull/3257))
+- Guard `.strip()` against None values from YAML config ([#3552](https://github.com/NousResearch/hermes-agent/pull/3552))
+- Guard `config.get()` against YAML null values to prevent AttributeError ([#3377](https://github.com/NousResearch/hermes-agent/pull/3377))
+- Store asyncio task references to prevent GC mid-execution ([#3267](https://github.com/NousResearch/hermes-agent/pull/3267))
+
+### Setup & Configuration
+- Use explicit key mapping for returning-user menu dispatch instead of positional index ([#3083](https://github.com/NousResearch/hermes-agent/pull/3083))
+- Use `sys.executable` for pip in update commands to fix PEP 668 ([#3099](https://github.com/NousResearch/hermes-agent/pull/3099))
+- Harden `hermes update` against diverged history, non-main branches, and gateway edge cases ([#3492](https://github.com/NousResearch/hermes-agent/pull/3492))
+- OpenClaw migration overwrites defaults and setup wizard skips imported sections — fixed ([#3282](https://github.com/NousResearch/hermes-agent/pull/3282))
+- Stop recursive AGENTS.md walk, load top-level only ([#3110](https://github.com/NousResearch/hermes-agent/pull/3110))
+- Add macOS Homebrew paths to browser and terminal PATH resolution ([#2713](https://github.com/NousResearch/hermes-agent/pull/2713))
+- YAML boolean handling for `tool_progress` config ([#3300](https://github.com/NousResearch/hermes-agent/pull/3300))
+- Reset default SOUL.md to baseline identity text ([#3159](https://github.com/NousResearch/hermes-agent/pull/3159))
+- Reject relative cwd paths for container terminal backends ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Add explicit `hermes-api-server` toolset for API server platform ([#3304](https://github.com/NousResearch/hermes-agent/pull/3304))
+- Reorder setup wizard providers — OpenRouter first ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+---
+
+## 🔧 Tool System
+
+### API Server
+- **Idempotency-Key support**, body size limit, and OpenAI error envelope ([#2903](https://github.com/NousResearch/hermes-agent/pull/2903))
+- Allow Idempotency-Key in CORS headers ([#3530](https://github.com/NousResearch/hermes-agent/pull/3530))
+- Cancel orphaned agent + true interrupt on SSE disconnect ([#3427](https://github.com/NousResearch/hermes-agent/pull/3427))
+- Fix streaming breaks when agent makes tool calls ([#2985](https://github.com/NousResearch/hermes-agent/pull/2985))
+
+### Terminal & File Operations
+- Handle addition-only hunks in V4A patch parser ([#3325](https://github.com/NousResearch/hermes-agent/pull/3325))
+- Exponential backoff for persistent shell polling ([#2996](https://github.com/NousResearch/hermes-agent/pull/2996))
+- Add timeout to subprocess calls in `context_references` ([#3469](https://github.com/NousResearch/hermes-agent/pull/3469))
+
+### Browser & Vision
+- Handle 402 insufficient credits error in vision tool ([#2802](https://github.com/NousResearch/hermes-agent/pull/2802))
+- Fix `browser_vision` ignores `auxiliary.vision.timeout` config ([#2901](https://github.com/NousResearch/hermes-agent/pull/2901))
+- Make browser command timeout configurable via config.yaml ([#2801](https://github.com/NousResearch/hermes-agent/pull/2801))
+
+### MCP
+- MCP toolset resolution for runtime and config ([#3252](https://github.com/NousResearch/hermes-agent/pull/3252))
+- Add MCP tool name collision protection ([#3077](https://github.com/NousResearch/hermes-agent/pull/3077))
+
+### Auxiliary LLM
+- Guard aux LLM calls against None content + reasoning fallback + retry ([#3449](https://github.com/NousResearch/hermes-agent/pull/3449))
+- Catch ImportError from `build_anthropic_client` in vision auto-detection ([#3312](https://github.com/NousResearch/hermes-agent/pull/3312))
+
+### Other Tools
+- Add request timeouts to `send_message_tool` HTTP calls ([#3162](https://github.com/NousResearch/hermes-agent/pull/3162)) by @memosr
+- Auto-repair `jobs.json` with invalid control characters ([#3537](https://github.com/NousResearch/hermes-agent/pull/3537))
+- Enable fine-grained tool streaming for Claude/OpenRouter ([#3497](https://github.com/NousResearch/hermes-agent/pull/3497))
+
+---
+
+## 🧩 Skills Ecosystem
+
+### Skills System
+- **Env var passthrough** for skills and user config — skills can declare environment variables to pass through ([#2807](https://github.com/NousResearch/hermes-agent/pull/2807))
+- Cache skills prompt with shared `skill_utils` module for faster TTFT ([#3421](https://github.com/NousResearch/hermes-agent/pull/3421))
+- Avoid redundant file re-read for skill conditions ([#2992](https://github.com/NousResearch/hermes-agent/pull/2992))
+- Use Git Trees API to prevent silent subdirectory loss during install ([#2995](https://github.com/NousResearch/hermes-agent/pull/2995))
+- Fix skills-sh install for deeply nested repo structures ([#2980](https://github.com/NousResearch/hermes-agent/pull/2980))
+- Handle null metadata in skill frontmatter ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Preserve trust for skills-sh identifiers + reduce resolution churn ([#3251](https://github.com/NousResearch/hermes-agent/pull/3251))
+- Agent-created skills were incorrectly treated as untrusted community content — fixed ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+### New Skills
+- **G0DM0D3 godmode jailbreaking skill** + docs ([#3157](https://github.com/NousResearch/hermes-agent/pull/3157))
+- **Docker management skill** added to optional-skills ([#3060](https://github.com/NousResearch/hermes-agent/pull/3060))
+- **OpenClaw migration v2** — 17 new modules, terminal recap for migrating from OpenClaw to Hermes ([#2906](https://github.com/NousResearch/hermes-agent/pull/2906))
+
+---
+
+## 🔒 Security & Reliability
+
+### Security Hardening
+- **SSRF protection** added to `browser_navigate` ([#3058](https://github.com/NousResearch/hermes-agent/pull/3058))
+- **SSRF protection** added to `vision_tools` and `web_tools` (hardened) ([#2679](https://github.com/NousResearch/hermes-agent/pull/2679))
+- **Restrict subagent toolsets** to parent's enabled set ([#3269](https://github.com/NousResearch/hermes-agent/pull/3269))
+- **Prevent zip-slip path traversal** in self-update ([#3250](https://github.com/NousResearch/hermes-agent/pull/3250))
+- **Prevent shell injection** in `_expand_path` via `~user` path suffix ([#2685](https://github.com/NousResearch/hermes-agent/pull/2685))
+- **Normalize input** before dangerous command detection ([#3260](https://github.com/NousResearch/hermes-agent/pull/3260))
+- Make tirith block verdicts approvable instead of hard-blocking ([#3428](https://github.com/NousResearch/hermes-agent/pull/3428))
+- Remove compromised `litellm`/`typer`/`platformdirs` from deps ([#2796](https://github.com/NousResearch/hermes-agent/pull/2796))
+- Pin all dependency version ranges ([#2810](https://github.com/NousResearch/hermes-agent/pull/2810))
+- Regenerate `uv.lock` with hashes, use lockfile in setup ([#2812](https://github.com/NousResearch/hermes-agent/pull/2812))
+- Bump dependencies to fix CVEs + regenerate `uv.lock` ([#3073](https://github.com/NousResearch/hermes-agent/pull/3073))
+- Supply chain audit CI workflow for PR scanning ([#2816](https://github.com/NousResearch/hermes-agent/pull/2816))
+
+### Reliability
+- **SQLite WAL write-lock contention** causing 15-20s TUI freeze — fixed ([#3385](https://github.com/NousResearch/hermes-agent/pull/3385))
+- **SQLite concurrency hardening** + session transcript integrity ([#3249](https://github.com/NousResearch/hermes-agent/pull/3249))
+- Prevent recurring cron job re-fire on gateway crash/restart loop ([#3396](https://github.com/NousResearch/hermes-agent/pull/3396))
+- Mark cron session as ended after job completes ([#2998](https://github.com/NousResearch/hermes-agent/pull/2998))
+
+---
+
+## ⚡ Performance
+
+- **TTFT startup optimizations** — salvaged easy-win startup improvements ([#3395](https://github.com/NousResearch/hermes-agent/pull/3395))
+- Cache skills prompt with shared `skill_utils` module ([#3421](https://github.com/NousResearch/hermes-agent/pull/3421))
+- Avoid redundant file re-read for skill conditions in prompt builder ([#2992](https://github.com/NousResearch/hermes-agent/pull/2992))
+
+---
+
+## 🐛 Notable Bug Fixes
+
+- Fix gateway token double-counting with cached agents ([#3306](https://github.com/NousResearch/hermes-agent/pull/3306), [#3317](https://github.com/NousResearch/hermes-agent/pull/3317))
+- Fix "Event loop is closed" / "Press ENTER to continue" during idle sessions ([#3398](https://github.com/NousResearch/hermes-agent/pull/3398))
+- Fix reasoning box rendering 3x during tool-calling loops ([#3405](https://github.com/NousResearch/hermes-agent/pull/3405))
+- Fix status bar shows 26K instead of 260K for token counts ([#3024](https://github.com/NousResearch/hermes-agent/pull/3024))
+- Fix `/queue` always working regardless of config ([#3298](https://github.com/NousResearch/hermes-agent/pull/3298))
+- Fix phantom Discord typing indicator after agent turn ([#3003](https://github.com/NousResearch/hermes-agent/pull/3003))
+- Fix Slack progress messages appearing in wrong thread ([#3063](https://github.com/NousResearch/hermes-agent/pull/3063))
+- Fix WhatsApp media downloads (documents, audio, video) ([#2978](https://github.com/NousResearch/hermes-agent/pull/2978))
+- Fix Telegram "Message thread not found" killing progress messages ([#3390](https://github.com/NousResearch/hermes-agent/pull/3390))
+- Fix OpenClaw migration overwriting defaults ([#3282](https://github.com/NousResearch/hermes-agent/pull/3282))
+- Fix returning-user setup menu dispatching wrong section ([#3083](https://github.com/NousResearch/hermes-agent/pull/3083))
+- Fix `hermes update` PEP 668 "externally-managed-environment" error ([#3099](https://github.com/NousResearch/hermes-agent/pull/3099))
+- Fix subagents hitting `max_iterations` prematurely via shared budget ([#3004](https://github.com/NousResearch/hermes-agent/pull/3004))
+- Fix YAML boolean handling for `tool_progress` config ([#3300](https://github.com/NousResearch/hermes-agent/pull/3300))
+- Fix `config.get()` crashes on YAML null values ([#3377](https://github.com/NousResearch/hermes-agent/pull/3377))
+- Fix `.strip()` crash on None values from YAML config ([#3552](https://github.com/NousResearch/hermes-agent/pull/3552))
+- Fix hung agents on gateway — `/stop` now hard-kills session lock ([#3104](https://github.com/NousResearch/hermes-agent/pull/3104))
+- Fix `_custom` provider silently remapped to `openrouter` ([#2792](https://github.com/NousResearch/hermes-agent/pull/2792))
+- Fix Matrix missing from `PLATFORMS` dict ([#3473](https://github.com/NousResearch/hermes-agent/pull/3473))
+- Fix Email adapter unbounded `_seen_uids` growth ([#3490](https://github.com/NousResearch/hermes-agent/pull/3490))
+
+---
+
+## 🧪 Testing
+
+- Pin `agent-client-protocol` < 0.9 to handle breaking upstream release ([#3320](https://github.com/NousResearch/hermes-agent/pull/3320))
+- Catch anthropic ImportError in vision auto-detection tests ([#3312](https://github.com/NousResearch/hermes-agent/pull/3312))
+- Update retry-exhaust test for new graceful return behavior ([#3320](https://github.com/NousResearch/hermes-agent/pull/3320))
+- Add regression tests for null metadata frontmatter ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+---
+
+## 📚 Documentation
+
+- Update all docs for `/model` command overhaul and custom provider support ([#2800](https://github.com/NousResearch/hermes-agent/pull/2800))
+- Fix stale and incorrect documentation across 18 files ([#2805](https://github.com/NousResearch/hermes-agent/pull/2805))
+- Document 9 previously undocumented features ([#2814](https://github.com/NousResearch/hermes-agent/pull/2814))
+- Add missing skills, CLI commands, and messaging env vars to docs ([#2809](https://github.com/NousResearch/hermes-agent/pull/2809))
+- Fix api-server response storage documentation — SQLite, not in-memory ([#2819](https://github.com/NousResearch/hermes-agent/pull/2819))
+- Quote pip install extras to fix zsh glob errors ([#2815](https://github.com/NousResearch/hermes-agent/pull/2815))
+- Unify hooks documentation — add plugin hooks to hooks page, add `session:end` event ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Clarify two-mode behavior in `session_search` schema description ([untagged commit](https://github.com/NousResearch/hermes-agent))
+- Fix Discord Public Bot setting for Discord-provided invite link ([#3519](https://github.com/NousResearch/hermes-agent/pull/3519)) by @mehmoodosman
+- Revise v0.4.0 changelog — fix feature attribution, reorder sections ([untagged commit](https://github.com/NousResearch/hermes-agent))
+
+---
+
+## 👥 Contributors
+
+### Core
+- **@teknium1** — 157 PRs covering the full scope of this release
+
+### Community Contributors
+- **@alt-glitch** (Siddharth Balyan) — 2 PRs: Nix flake with uv2nix build, NixOS module, and persistent container mode ([#20](https://github.com/NousResearch/hermes-agent/pull/20)); auto-generated config keys and suffix PATHs for Nix builds ([#3061](https://github.com/NousResearch/hermes-agent/pull/3061), [#3274](https://github.com/NousResearch/hermes-agent/pull/3274))
+- **@ctlst** — 1 PR: Prevent AsyncOpenAI/httpx cross-loop deadlock in gateway mode ([#2701](https://github.com/NousResearch/hermes-agent/pull/2701))
+- **@memosr** (memosr.eth) — 1 PR: Add request timeouts to `send_message_tool` HTTP calls ([#3162](https://github.com/NousResearch/hermes-agent/pull/3162))
+- **@mehmoodosman** (Osman Mehmood) — 1 PR: Fix Discord docs for Public Bot setting ([#3519](https://github.com/NousResearch/hermes-agent/pull/3519))
+
+### All Contributors
+@alt-glitch, @ctlst, @mehmoodosman, @memosr, @teknium1
+
+---
+
+**Full Changelog**: [v2026.3.23...v2026.3.28](https://github.com/NousResearch/hermes-agent/compare/v2026.3.23...v2026.3.28)
@@ -35,6 +35,54 @@ ADAPTIVE_EFFORT_MAP = {
    "minimal": "low",
 }

+# ── Max output token limits per Anthropic model ───────────────────────
+# Source: Anthropic docs + Cline model catalog.  Anthropic's API requires
+# max_tokens as a mandatory field.  Previously we hardcoded 16384, which
+# starves thinking-enabled models (thinking tokens count toward the limit).
+_ANTHROPIC_OUTPUT_LIMITS = {
+    # Claude 4.6
+    "claude-opus-4-6":   128_000,
+    "claude-sonnet-4-6":  64_000,
+    # Claude 4.5
+    "claude-opus-4-5":    64_000,
+    "claude-sonnet-4-5":  64_000,
+    "claude-haiku-4-5":   64_000,
+    # Claude 4
+    "claude-opus-4":      32_000,
+    "claude-sonnet-4":    64_000,
+    # Claude 3.7
+    "claude-3-7-sonnet": 128_000,
+    # Claude 3.5
+    "claude-3-5-sonnet":   8_192,
+    "claude-3-5-haiku":    8_192,
+    # Claude 3
+    "claude-3-opus":       4_096,
+    "claude-3-sonnet":     4_096,
+    "claude-3-haiku":      4_096,
+}
+
+# For any model not in the table, assume the highest current limit.
+# Future Anthropic models are unlikely to have *less* output capacity.
+_ANTHROPIC_DEFAULT_OUTPUT_LIMIT = 128_000
+
+
+def _get_anthropic_max_output(model: str) -> int:
+    """Look up the max output token limit for an Anthropic model.
+
+    Uses substring matching against _ANTHROPIC_OUTPUT_LIMITS so date-stamped
+    model IDs (claude-sonnet-4-5-20250929) and variant suffixes (:1m, :fast)
+    resolve correctly.  Longest-prefix match wins to avoid e.g. "claude-3-5"
+    matching before "claude-3-5-sonnet".
+    """
+    m = model.lower()
+    best_key = ""
+    best_val = _ANTHROPIC_DEFAULT_OUTPUT_LIMIT
+    for key, val in _ANTHROPIC_OUTPUT_LIMITS.items():
+        if key in m and len(key) > len(best_key):
+            best_key = key
+            best_val = val
+    return best_val
+

 def _supports_adaptive_thinking(model: str) -> bool:
    """Return True for Claude 4.6 models that support adaptive thinking."""
@@ -59,6 +107,7 @@ _OAUTH_ONLY_BETAS = [
 # The version must stay reasonably current — Anthropic rejects OAuth requests
 # when the spoofed user-agent version is too far behind the actual release.
 _CLAUDE_CODE_VERSION_FALLBACK = "2.1.74"
+_claude_code_version_cache: Optional[str] = None


 def _detect_claude_code_version() -> str:
@@ -86,11 +135,18 @@ def _detect_claude_code_version() -> str:
    return _CLAUDE_CODE_VERSION_FALLBACK


-_CLAUDE_CODE_VERSION = _detect_claude_code_version()
 _CLAUDE_CODE_SYSTEM_PREFIX = "You are Claude Code, Anthropic's official CLI for Claude."
 _MCP_TOOL_PREFIX = "mcp_"


+def _get_claude_code_version() -> str:
+    """Lazily detect the installed Claude Code version when OAuth headers need it."""
+    global _claude_code_version_cache
+    if _claude_code_version_cache is None:
+        _claude_code_version_cache = _detect_claude_code_version()
+    return _claude_code_version_cache
+
+
 def _is_oauth_token(key: str) -> bool:
    """Check if the key is an OAuth/setup token (not a regular Console API key).

@@ -132,7 +188,7 @@ def build_anthropic_client(api_key: str, base_url: str = None):
        kwargs["auth_token"] = api_key
        kwargs["default_headers"] = {
            "anthropic-beta": ",".join(all_betas),
-            "user-agent": f"claude-cli/{_CLAUDE_CODE_VERSION} (external, cli)",
+            "user-agent": f"claude-cli/{_get_claude_code_version()} (external, cli)",
            "x-app": "cli",
        }
    else:
@@ -241,7 +297,7 @@ def _refresh_oauth_token(creds: Dict[str, Any]) -> Optional[str]:

    headers = {
        "Content-Type": "application/json",
-        "User-Agent": f"claude-cli/{_CLAUDE_CODE_VERSION} (external, cli)",
+        "User-Agent": f"claude-cli/{_get_claude_code_version()} (external, cli)",
    }

    for endpoint in token_endpoints:
@@ -706,14 +762,21 @@ def convert_messages_to_anthropic(
                result.append({"role": "user", "content": [tool_result]})
            continue

-        # Regular user message
+        # Regular user message — validate non-empty content (Anthropic rejects empty)
        if isinstance(content, list):
            converted_blocks = _convert_content_to_anthropic(content)
-            result.append({
-                "role": "user",
-                "content": converted_blocks or [{"type": "text", "text": ""}],
-            })
+            # Check if all text blocks are empty
+            if not converted_blocks or all(
+                b.get("text", "").strip() == ""
+                for b in converted_blocks
+                if isinstance(b, dict) and b.get("type") == "text"
+            ):
+                converted_blocks = [{"type": "text", "text": "(empty message)"}]
+            result.append({"role": "user", "content": converted_blocks})
        else:
+            # Validate string content is non-empty
+            if not content or (isinstance(content, str) and not content.strip()):
+                content = "(empty message)"
            result.append({"role": "user", "content": content})

    # Strip orphaned tool_use blocks (no matching tool_result follows)
@@ -803,9 +866,15 @@ def build_anthropic_kwargs(
    tool_choice: Optional[str] = None,
    is_oauth: bool = False,
    preserve_dots: bool = False,
+    context_length: Optional[int] = None,
 ) -> Dict[str, Any]:
    """Build kwargs for anthropic.messages.create().

+    When *max_tokens* is None, the model's native output limit is used
+    (e.g. 128K for Opus 4.6, 64K for Sonnet 4.6).  If *context_length*
+    is provided, the effective limit is clamped so it doesn't exceed
+    the context window.
+
    When *is_oauth* is True, applies Claude Code compatibility transforms:
    system prompt prefix, tool name prefixing, and prompt sanitization.

@@ -816,7 +885,12 @@ def build_anthropic_kwargs(
    anthropic_tools = convert_tools_to_anthropic(tools) if tools else []

    model = normalize_model_name(model, preserve_dots=preserve_dots)
-    effective_max_tokens = max_tokens or 16384
+    effective_max_tokens = max_tokens or _get_anthropic_max_output(model)
+
+    # Clamp to context window if the user set a lower context_length
+    # (e.g. custom endpoint with limited capacity).
+    if context_length and effective_max_tokens > context_length:
+        effective_max_tokens = max(context_length - 1, 1)

    # ── OAuth: Claude Code identity ──────────────────────────────────
    if is_oauth:
@@ -693,7 +693,13 @@ def _try_anthropic() -> Tuple[Optional[Any], Optional[str]]:
    is_oauth = _is_oauth_token(token)
    model = _API_KEY_PROVIDER_AUX_MODELS.get("anthropic", "claude-haiku-4-5-20251001")
    logger.debug("Auxiliary client: Anthropic native (%s) at %s (oauth=%s)", model, base_url, is_oauth)
-    real_client = build_anthropic_client(token, base_url)
+    try:
+        real_client = build_anthropic_client(token, base_url)
+    except ImportError:
+        # The anthropic_adapter module imports fine but the SDK itself is
+        # missing — build_anthropic_client raises ImportError at call time
+        # when _anthropic_sdk is None.  Treat as unavailable.
+        return None, None
    return AnthropicAuxiliaryClient(real_client, model, token, base_url, is_oauth=is_oauth), model


@@ -1131,7 +1137,13 @@ def resolve_vision_provider_client(
        return "custom", client, final_model

    if requested == "auto":
-        for candidate in get_available_vision_backends():
+        ordered = list(_VISION_AUTO_PROVIDER_ORDER)
+        preferred = _preferred_main_vision_provider()
+        if preferred in ordered:
+            ordered.remove(preferred)
+            ordered.insert(0, preferred)
+
+        for candidate in ordered:
            sync_client, default_model = _resolve_strict_vision_backend(candidate)
            if sync_client is not None:
                return _finalize(candidate, sync_client, default_model)
@@ -1204,6 +1216,39 @@ _client_cache: Dict[tuple, tuple] = {}
 _client_cache_lock = threading.Lock()


+def neuter_async_httpx_del() -> None:
+    """Monkey-patch ``AsyncHttpxClientWrapper.__del__`` to be a no-op.
+
+    The OpenAI SDK's ``AsyncHttpxClientWrapper.__del__`` schedules
+    ``self.aclose()`` via ``asyncio.get_running_loop().create_task()``.
+    When an ``AsyncOpenAI`` client is garbage-collected while
+    prompt_toolkit's event loop is running (the common CLI idle state),
+    the ``aclose()`` task runs on prompt_toolkit's loop but the
+    underlying TCP transport is bound to a *different* loop (the worker
+    thread's loop that the client was originally created on).  If that
+    loop is closed or its thread is dead, the transport's
+    ``self._loop.call_soon()`` raises ``RuntimeError("Event loop is
+    closed")``, which prompt_toolkit surfaces as "Unhandled exception
+    in event loop ... Press ENTER to continue...".
+
+    Neutering ``__del__`` is safe because:
+    - Cached clients are explicitly cleaned via ``_force_close_async_httpx``
+      on stale-loop detection and ``shutdown_cached_clients`` on exit.
+    - Uncached clients' TCP connections are cleaned up by the OS when the
+      process exits.
+    - The OpenAI SDK itself marks this as a TODO (``# TODO(someday):
+      support non asyncio runtimes here``).
+
+    Call this once at CLI startup, before any ``AsyncOpenAI`` clients are
+    created.
+    """
+    try:
+        from openai._base_client import AsyncHttpxClientWrapper
+        AsyncHttpxClientWrapper.__del__ = lambda self: None  # type: ignore[assignment]
+    except (ImportError, AttributeError):
+        pass  # Graceful degradation if the SDK changes its internals
+
+
 def _force_close_async_httpx(client: Any) -> None:
    """Mark the httpx AsyncClient inside an AsyncOpenAI client as closed.

@@ -1251,6 +1296,25 @@ def shutdown_cached_clients() -> None:
        _client_cache.clear()


+def cleanup_stale_async_clients() -> None:
+    """Force-close cached async clients whose event loop is closed.
+
+    Call this after each agent turn to proactively clean up stale clients
+    before GC can trigger ``AsyncHttpxClientWrapper.__del__`` on them.
+    This is defense-in-depth — the primary fix is ``neuter_async_httpx_del``
+    which disables ``__del__`` entirely.
+    """
+    with _client_cache_lock:
+        stale_keys = []
+        for key, entry in _client_cache.items():
+            client, _default, cached_loop = entry
+            if cached_loop is not None and cached_loop.is_closed():
+                _force_close_async_httpx(client)
+                stale_keys.append(key)
+        for key in stale_keys:
+            del _client_cache[key]
+
+
 def _get_cached_client(
    provider: str,
    model: str = None,
@@ -1394,6 +1458,29 @@ def _resolve_task_provider_model(
    return "auto", resolved_model, None, None


+_DEFAULT_AUX_TIMEOUT = 30.0
+
+
+def _get_task_timeout(task: str, default: float = _DEFAULT_AUX_TIMEOUT) -> float:
+    """Read timeout from auxiliary.{task}.timeout in config, falling back to *default*."""
+    if not task:
+        return default
+    try:
+        from hermes_cli.config import load_config
+        config = load_config()
+    except ImportError:
+        return default
+    aux = config.get("auxiliary", {}) if isinstance(config, dict) else {}
+    task_config = aux.get(task, {}) if isinstance(aux, dict) else {}
+    raw = task_config.get("timeout")
+    if raw is not None:
+        try:
+            return float(raw)
+        except (ValueError, TypeError):
+            pass
+    return default
+
+
 def _build_call_kwargs(
    provider: str,
    model: str,
@@ -1451,7 +1538,7 @@ def call_llm(
    temperature: float = None,
    max_tokens: int = None,
    tools: list = None,
-    timeout: float = 30.0,
+    timeout: float = None,
    extra_body: dict = None,
 ) -> Any:
    """Centralized synchronous LLM call.
@@ -1469,7 +1556,7 @@ def call_llm(
        temperature: Sampling temperature (None = provider default).
        max_tokens: Max output tokens (handles max_tokens vs max_completion_tokens).
        tools: Tool definitions (for function calling).
-        timeout: Request timeout in seconds.
+        timeout: Request timeout in seconds (None = read from auxiliary.{task}.timeout config).
        extra_body: Additional request body fields.

    Returns:
@@ -1534,10 +1621,12 @@ def call_llm(
                f"No LLM provider configured for task={task} provider={resolved_provider}. "
                f"Run: hermes setup")

+    effective_timeout = timeout if timeout is not None else _get_task_timeout(task)
+
    kwargs = _build_call_kwargs(
        resolved_provider, final_model, messages,
        temperature=temperature, max_tokens=max_tokens,
-        tools=tools, timeout=timeout, extra_body=extra_body,
+        tools=tools, timeout=effective_timeout, extra_body=extra_body,
        base_url=resolved_base_url)

    # Handle max_tokens vs max_completion_tokens retry
@@ -1552,6 +1641,62 @@ def call_llm(
        raise


+def extract_content_or_reasoning(response) -> str:
+    """Extract content from an LLM response, falling back to reasoning fields.
+
+    Mirrors the main agent loop's behavior when a reasoning model (DeepSeek-R1,
+    Qwen-QwQ, etc.) returns ``content=None`` with reasoning in structured fields.
+
+    Resolution order:
+      1. ``message.content`` — strip inline think/reasoning blocks, check for
+         remaining non-whitespace text.
+      2. ``message.reasoning`` / ``message.reasoning_content`` — direct
+         structured reasoning fields (DeepSeek, Moonshot, Novita, etc.).
+      3. ``message.reasoning_details`` — OpenRouter unified array format.
+
+    Returns the best available text, or ``""`` if nothing found.
+    """
+    import re
+
+    msg = response.choices[0].message
+    content = (msg.content or "").strip()
+
+    if content:
+        # Strip inline think/reasoning blocks (mirrors _strip_think_blocks)
+        cleaned = re.sub(
+            r"<(?:think|thinking|reasoning|REASONING_SCRATCHPAD)>"
+            r".*?"
+            r"</(?:think|thinking|reasoning|REASONING_SCRATCHPAD)>",
+            "", content, flags=re.DOTALL | re.IGNORECASE,
+        ).strip()
+        if cleaned:
+            return cleaned
+
+    # Content is empty or reasoning-only — try structured reasoning fields
+    reasoning_parts: list[str] = []
+    for field in ("reasoning", "reasoning_content"):
+        val = getattr(msg, field, None)
+        if val and isinstance(val, str) and val.strip() and val not in reasoning_parts:
+            reasoning_parts.append(val.strip())
+
+    details = getattr(msg, "reasoning_details", None)
+    if details and isinstance(details, list):
+        for detail in details:
+            if isinstance(detail, dict):
+                summary = (
+                    detail.get("summary")
+                    or detail.get("content")
+                    or detail.get("text")
+                )
+                if summary and summary not in reasoning_parts:
+                    reasoning_parts.append(summary.strip() if isinstance(summary, str) else str(summary))
+
+    if reasoning_parts:
+        return "\n\n".join(reasoning_parts)
+
+    return ""
+
+
 async def async_call_llm(
    task: str = None,
    *,
@@ -1563,7 +1708,7 @@ async def async_call_llm(
    temperature: float = None,
    max_tokens: int = None,
    tools: list = None,
-    timeout: float = 30.0,
+    timeout: float = None,
    extra_body: dict = None,
 ) -> Any:
    """Centralized asynchronous LLM call.
@@ -1624,10 +1769,12 @@ async def async_call_llm(
                f"No LLM provider configured for task={task} provider={resolved_provider}. "
                f"Run: hermes setup")

+    effective_timeout = timeout if timeout is not None else _get_task_timeout(task)
+
    kwargs = _build_call_kwargs(
        resolved_provider, final_model, messages,
        temperature=temperature, max_tokens=max_tokens,
-        tools=tools, timeout=timeout, extra_body=extra_body,
+        tools=tools, timeout=effective_timeout, extra_body=extra_body,
        base_url=resolved_base_url)

    try:
@@ -141,7 +141,7 @@ class ContextCompressor:
            "last_prompt_tokens": self.last_prompt_tokens,
            "threshold_tokens": self.threshold_tokens,
            "context_length": self.context_length,
-            "usage_percent": (self.last_prompt_tokens / self.context_length * 100) if self.context_length else 0,
+            "usage_percent": min(100, (self.last_prompt_tokens / self.context_length * 100)) if self.context_length else 0,
            "compression_count": self.compression_count,
        }

@@ -347,7 +347,7 @@ Write only the summary body. Do not include any preamble or prefix."""
                "messages": [{"role": "user", "content": prompt}],
                "temperature": 0.3,
                "max_tokens": summary_budget * 2,
-                "timeout": 45.0,
+                # timeout resolved from auxiliary.compression.timeout config by call_llm
            }
            if self.summary_model:
                call_kwargs["model"] = self.summary_model
@@ -286,12 +286,16 @@ def _expand_git_reference(
    args: list[str],
    label: str,
 ) -> tuple[str | None, str | None]:
-    result = subprocess.run(
-        ["git", *args],
-        cwd=cwd,
-        capture_output=True,
-        text=True,
-    )
+    try:
+        result = subprocess.run(
+            ["git", *args],
+            cwd=cwd,
+            capture_output=True,
+            text=True,
+            timeout=30,
+        )
+    except subprocess.TimeoutExpired:
+        return f"{ref.raw}: git command timed out (30s)", None
    if result.returncode != 0:
        stderr = (result.stderr or "").strip() or "git command failed"
        return f"{ref.raw}: {stderr}", None
@@ -449,9 +453,12 @@ def _rg_files(path: Path, cwd: Path, limit: int) -> list[Path] | None:
            cwd=cwd,
            capture_output=True,
            text=True,
+            timeout=10,
        )
    except FileNotFoundError:
        return None
+    except subprocess.TimeoutExpired:
+        return None
    if result.returncode != 0:
        return None
    files = [Path(line.strip()) for line in result.stdout.splitlines() if line.strip()]
@@ -231,7 +231,7 @@ class KawaiiSpinner:
        "analyzing", "computing", "synthesizing", "formulating", "brainstorming",
    ]

-    def __init__(self, message: str = "", spinner_type: str = 'dots'):
+    def __init__(self, message: str = "", spinner_type: str = 'dots', print_fn=None):
        self.message = message
        self.spinner_frames = self.SPINNERS.get(spinner_type, self.SPINNERS['dots'])
        self.running = False
@@ -239,12 +239,26 @@ class KawaiiSpinner:
        self.frame_idx = 0
        self.start_time = None
        self.last_line_len = 0
+        # Optional callable to route all output through (e.g. a no-op for silent
+        # background agents).  When set, bypasses self._out entirely so that
+        # agents with _print_fn overridden remain fully silent.
+        self._print_fn = print_fn
        # Capture stdout NOW, before any redirect_stdout(devnull) from
        # child agents can replace sys.stdout with a black hole.
        self._out = sys.stdout

    def _write(self, text: str, end: str = '\n', flush: bool = False):
-        """Write to the stdout captured at spinner creation time."""
+        """Write to the stdout captured at spinner creation time.
+
+        If a print_fn was supplied at construction, all output is routed through
+        it instead — allowing callers to silence the spinner with a no-op lambda.
+        """
+        if self._print_fn is not None:
+            try:
+                self._print_fn(text)
+            except Exception:
+                pass
+            return
        try:
            self._out.write(text + end)
            if flush:
@@ -270,11 +284,11 @@ class KawaiiSpinner:
        The CLI already drives a TUI widget (_spinner_text) for spinner display,
        so KawaiiSpinner's \\r-based animation is redundant under StdoutProxy.
        """
-        out = self._out
-        # StdoutProxy has a 'raw' attribute (bool) that plain file objects lack.
-        if hasattr(out, 'raw') and type(out).__name__ == 'StdoutProxy':
-            return True
-        return False
+        try:
+            from prompt_toolkit.patch_stdout import StdoutProxy
+            return isinstance(self._out, StdoutProxy)
+        except ImportError:
+            return False

    def _animate(self):
        # When stdout is not a real terminal (e.g. Docker, systemd, pipe),
@@ -685,7 +699,7 @@ def format_context_pressure(
        threshold_percent: Compaction threshold as a fraction of context window.
        compression_enabled: Whether auto-compression is active.
    """
-    pct_int = int(compaction_progress * 100)
+    pct_int = min(int(compaction_progress * 100), 100)
    filled = min(int(compaction_progress * _BAR_WIDTH), _BAR_WIDTH)
    bar = _BAR_FILLED * filled + _BAR_EMPTY * (_BAR_WIDTH - filled)

@@ -715,7 +729,7 @@ def format_context_pressure_gateway(
    No ANSI — just Unicode and plain text suitable for Telegram/Discord/etc.
    The percentage shows progress toward the compaction threshold.
    """
-    pct_int = int(compaction_progress * 100)
+    pct_int = min(int(compaction_progress * 100), 100)
    filled = min(int(compaction_progress * _BAR_WIDTH), _BAR_WIDTH)
    bar = _BAR_FILLED * filled + _BAR_EMPTY * (_BAR_WIDTH - filled)

@@ -113,6 +113,15 @@ DEFAULT_CONTEXT_LENGTHS = {
    "glm": 202752,
    # Kimi
    "kimi": 262144,
+    # Hugging Face Inference Providers — model IDs use org/name format
+    "Qwen/Qwen3.5-397B-A17B": 131072,
+    "Qwen/Qwen3.5-35B-A3B": 131072,
+    "deepseek-ai/DeepSeek-V3.2": 65536,
+    "moonshotai/Kimi-K2.5": 262144,
+    "moonshotai/Kimi-K2-Thinking": 262144,
+    "MiniMaxAI/MiniMax-M2.5": 204800,
+    "XiaomiMiMo/MiMo-V2-Flash": 32768,
+    "zai-org/GLM-5": 202752,
 }

 _CONTEXT_LENGTH_KEYS = (
@@ -15,6 +15,8 @@ import time
 from pathlib import Path
 from typing import Any, Dict, Optional

+from utils import atomic_json_write
+
 import requests

 logger = logging.getLogger(__name__)
@@ -64,12 +66,10 @@ def _load_disk_cache() -> Dict[str, Any]:


 def _save_disk_cache(data: Dict[str, Any]) -> None:
-    """Save models.dev data to disk cache."""
+    """Save models.dev data to disk cache atomically."""
    try:
        cache_path = _get_cache_path()
-        cache_path.parent.mkdir(parents=True, exist_ok=True)
-        with open(cache_path, "w", encoding="utf-8") as f:
-            json.dump(data, f, separators=(",", ":"))
+        atomic_json_write(cache_path, data, indent=None, separators=(",", ":"))
    except Exception as e:
        logger.debug("Failed to save models.dev disk cache: %s", e)

@@ -4,14 +4,27 @@ All functions are stateless. AIAgent._build_system_prompt() calls these to
 assemble pieces, then combines them with memory and ephemeral prompts.
 """

+import json
 import logging
 import os
 import re
+import threading
+from collections import OrderedDict
 from pathlib import Path

 from hermes_constants import get_hermes_home
 from typing import Optional

+from agent.skill_utils import (
+    extract_skill_conditions,
+    extract_skill_description,
+    get_disabled_skill_names,
+    iter_skill_index_files,
+    parse_frontmatter,
+    skill_matches_platform,
+)
+from utils import atomic_json_write
+
 logger = logging.getLogger(__name__)

 # ---------------------------------------------------------------------------
@@ -156,6 +169,25 @@ SKILLS_GUIDANCE = (
    "Skills that aren't maintained become liabilities."
 )

+TOOL_USE_ENFORCEMENT_GUIDANCE = (
+    "# Tool-use enforcement\n"
+    "You MUST use your tools to take action — do not describe what you would do "
+    "or plan to do without actually doing it. When you say you will perform an "
+    "action (e.g. 'I will run the tests', 'Let me check the file', 'I will create "
+    "the project'), you MUST immediately make the corresponding tool call in the same "
+    "response. Never end your turn with a promise of future action — execute it now.\n"
+    "Keep working until the task is actually complete. Do not stop with a summary of "
+    "what you plan to do next time. If you have tools available that can accomplish "
+    "the task, use them instead of telling the user what you would do.\n"
+    "Every response should either (a) contain tool calls that make progress, or "
+    "(b) deliver a final result to the user. Responses that only describe intentions "
+    "without acting are not acceptable."
+)
+
+# Model name substrings that trigger tool-use enforcement guidance.
+# Add new patterns here when a model family needs explicit steering.
+TOOL_USE_ENFORCEMENT_MODELS = ("gpt", "codex")
+
 PLATFORM_HINTS = {
    "whatsapp": (
        "You are on a text messaging communication platform, WhatsApp. "
@@ -230,6 +262,111 @@ CONTEXT_TRUNCATE_HEAD_RATIO = 0.7
 CONTEXT_TRUNCATE_TAIL_RATIO = 0.2


+# =========================================================================
+# Skills prompt cache
+# =========================================================================
+
+_SKILLS_PROMPT_CACHE_MAX = 8
+_SKILLS_PROMPT_CACHE: OrderedDict[tuple, str] = OrderedDict()
+_SKILLS_PROMPT_CACHE_LOCK = threading.Lock()
+_SKILLS_SNAPSHOT_VERSION = 1
+
+
+def _skills_prompt_snapshot_path() -> Path:
+    return get_hermes_home() / ".skills_prompt_snapshot.json"
+
+
+def clear_skills_system_prompt_cache(*, clear_snapshot: bool = False) -> None:
+    """Drop the in-process skills prompt cache (and optionally the disk snapshot)."""
+    with _SKILLS_PROMPT_CACHE_LOCK:
+        _SKILLS_PROMPT_CACHE.clear()
+    if clear_snapshot:
+        try:
+            _skills_prompt_snapshot_path().unlink(missing_ok=True)
+        except OSError as e:
+            logger.debug("Could not remove skills prompt snapshot: %s", e)
+
+
+def _build_skills_manifest(skills_dir: Path) -> dict[str, list[int]]:
+    """Build an mtime/size manifest of all SKILL.md and DESCRIPTION.md files."""
+    manifest: dict[str, list[int]] = {}
+    for filename in ("SKILL.md", "DESCRIPTION.md"):
+        for path in iter_skill_index_files(skills_dir, filename):
+            try:
+                st = path.stat()
+            except OSError:
+                continue
+            manifest[str(path.relative_to(skills_dir))] = [st.st_mtime_ns, st.st_size]
+    return manifest
+
+
+def _load_skills_snapshot(skills_dir: Path) -> Optional[dict]:
+    """Load the disk snapshot if it exists and its manifest still matches."""
+    snapshot_path = _skills_prompt_snapshot_path()
+    if not snapshot_path.exists():
+        return None
+    try:
+        snapshot = json.loads(snapshot_path.read_text(encoding="utf-8"))
+    except Exception:
+        return None
+    if not isinstance(snapshot, dict):
+        return None
+    if snapshot.get("version") != _SKILLS_SNAPSHOT_VERSION:
+        return None
+    if snapshot.get("manifest") != _build_skills_manifest(skills_dir):
+        return None
+    return snapshot
+
+
+def _write_skills_snapshot(
+    skills_dir: Path,
+    manifest: dict[str, list[int]],
+    skill_entries: list[dict],
+    category_descriptions: dict[str, str],
+) -> None:
+    """Persist skill metadata to disk for fast cold-start reuse."""
+    payload = {
+        "version": _SKILLS_SNAPSHOT_VERSION,
+        "manifest": manifest,
+        "skills": skill_entries,
+        "category_descriptions": category_descriptions,
+    }
+    try:
+        atomic_json_write(_skills_prompt_snapshot_path(), payload)
+    except Exception as e:
+        logger.debug("Could not write skills prompt snapshot: %s", e)
+
+
+def _build_snapshot_entry(
+    skill_file: Path,
+    skills_dir: Path,
+    frontmatter: dict,
+    description: str,
+) -> dict:
+    """Build a serialisable metadata dict for one skill."""
+    rel_path = skill_file.relative_to(skills_dir)
+    parts = rel_path.parts
+    if len(parts) >= 2:
+        skill_name = parts[-2]
+        category = "/".join(parts[:-2]) if len(parts) > 2 else parts[0]
+    else:
+        category = "general"
+        skill_name = skill_file.parent.name
+
+    platforms = frontmatter.get("platforms") or []
+    if isinstance(platforms, str):
+        platforms = [platforms]
+
+    return {
+        "skill_name": skill_name,
+        "category": category,
+        "frontmatter_name": str(frontmatter.get("name", skill_name)),
+        "description": description,
+        "platforms": [str(p).strip() for p in platforms if str(p).strip()],
+        "conditions": extract_skill_conditions(frontmatter),
+    }
+
+
 # =========================================================================
 # Skills index
 # =========================================================================
@@ -241,22 +378,13 @@ def _parse_skill_file(skill_file: Path) -> tuple[bool, dict, str]:
    (True, {}, "") to err on the side of showing the skill.
    """
    try:
-        from tools.skills_tool import _parse_frontmatter, skill_matches_platform
-
        raw = skill_file.read_text(encoding="utf-8")[:2000]
-        frontmatter, _ = _parse_frontmatter(raw)
+        frontmatter, _ = parse_frontmatter(raw)

        if not skill_matches_platform(frontmatter):
-            return False, {}, ""
+            return False, frontmatter, ""

-        desc = ""
-        raw_desc = frontmatter.get("description", "")
-        if raw_desc:
-            desc = str(raw_desc).strip().strip("'\"")
-            if len(desc) > 60:
-                desc = desc[:57] + "..."
-
-        return True, frontmatter, desc
+        return True, frontmatter, extract_skill_description(frontmatter)
    except Exception as e:
        logger.debug("Failed to parse skill file %s: %s", skill_file, e)
        return True, {}, ""
@@ -265,16 +393,9 @@ def _parse_skill_file(skill_file: Path) -> tuple[bool, dict, str]:
 def _read_skill_conditions(skill_file: Path) -> dict:
    """Extract conditional activation fields from SKILL.md frontmatter."""
    try:
-        from tools.skills_tool import _parse_frontmatter
        raw = skill_file.read_text(encoding="utf-8")[:2000]
-        frontmatter, _ = _parse_frontmatter(raw)
-        hermes = frontmatter.get("metadata", {}).get("hermes", {})
-        return {
-            "fallback_for_toolsets": hermes.get("fallback_for_toolsets", []),
-            "requires_toolsets": hermes.get("requires_toolsets", []),
-            "fallback_for_tools": hermes.get("fallback_for_tools", []),
-            "requires_tools": hermes.get("requires_tools", []),
-        }
+        frontmatter, _ = parse_frontmatter(raw)
+        return extract_skill_conditions(frontmatter)
    except Exception as e:
        logger.debug("Failed to read skill conditions from %s: %s", skill_file, e)
        return {}
@@ -317,10 +438,12 @@ def build_skills_system_prompt(
 ) -> str:
    """Build a compact skill index for the system prompt.

-    Scans ~/.hermes/skills/ for SKILL.md files grouped by category.
-    Includes per-skill descriptions from frontmatter so the model can
-    match skills by meaning, not just name.
-    Filters out skills incompatible with the current OS platform.
+    Two-layer cache:
+      1. In-process LRU dict keyed by (skills_dir, tools, toolsets)
+      2. Disk snapshot (``.skills_prompt_snapshot.json``) validated by
+         mtime/size manifest — survives process restarts
+
+    Falls back to a full filesystem scan when both layers miss.
    """
    hermes_home = get_hermes_home()
    skills_dir = hermes_home / "skills"
@@ -328,98 +451,140 @@ def build_skills_system_prompt(
    if not skills_dir.exists():
        return ""

-    # Collect skills with descriptions, grouped by category.
-    # Each entry: (skill_name, description)
-    # Supports sub-categories: skills/mlops/training/axolotl/SKILL.md
-    # -> category "mlops/training", skill "axolotl"
-    # Load disabled skill names once for the entire scan
-    try:
-        from tools.skills_tool import _get_disabled_skill_names
-        disabled = _get_disabled_skill_names()
-    except Exception:
-        disabled = set()
+    # ── Layer 1: in-process LRU cache ─────────────────────────────────
+    cache_key = (
+        str(skills_dir.resolve()),
+        tuple(sorted(str(t) for t in (available_tools or set()))),
+        tuple(sorted(str(ts) for ts in (available_toolsets or set()))),
+    )
+    with _SKILLS_PROMPT_CACHE_LOCK:
+        cached = _SKILLS_PROMPT_CACHE.get(cache_key)
+        if cached is not None:
+            _SKILLS_PROMPT_CACHE.move_to_end(cache_key)
+            return cached
+
+    disabled = get_disabled_skill_names()
+
+    # ── Layer 2: disk snapshot ────────────────────────────────────────
+    snapshot = _load_skills_snapshot(skills_dir)

    skills_by_category: dict[str, list[tuple[str, str]]] = {}
-    for skill_file in skills_dir.rglob("SKILL.md"):
-        is_compatible, frontmatter, desc = _parse_skill_file(skill_file)
-        if not is_compatible:
-            continue
-        rel_path = skill_file.relative_to(skills_dir)
-        parts = rel_path.parts
-        if len(parts) >= 2:
-            skill_name = parts[-2]
-            category = "/".join(parts[:-2]) if len(parts) > 2 else parts[0]
-        else:
-            category = "general"
-            skill_name = skill_file.parent.name
-        # Respect user's disabled skills config
-        fm_name = frontmatter.get("name", skill_name)
-        if fm_name in disabled or skill_name in disabled:
-            continue
-        # Extract conditions inline from already-parsed frontmatter
-        # (avoids redundant file re-read that _read_skill_conditions would do)
-        hermes_meta = (frontmatter.get("metadata") or {}).get("hermes") or {}
-        conditions = {
-            "fallback_for_toolsets": hermes_meta.get("fallback_for_toolsets", []),
-            "requires_toolsets": hermes_meta.get("requires_toolsets", []),
-            "fallback_for_tools": hermes_meta.get("fallback_for_tools", []),
-            "requires_tools": hermes_meta.get("requires_tools", []),
+    category_descriptions: dict[str, str] = {}
+
+    if snapshot is not None:
+        # Fast path: use pre-parsed metadata from disk
+        for entry in snapshot.get("skills", []):
+            if not isinstance(entry, dict):
+                continue
+            skill_name = entry.get("skill_name") or ""
+            category = entry.get("category") or "general"
+            frontmatter_name = entry.get("frontmatter_name") or skill_name
+            platforms = entry.get("platforms") or []
+            if not skill_matches_platform({"platforms": platforms}):
+                continue
+            if frontmatter_name in disabled or skill_name in disabled:
+                continue
+            if not _skill_should_show(
+                entry.get("conditions") or {},
+                available_tools,
+                available_toolsets,
+            ):
+                continue
+            skills_by_category.setdefault(category, []).append(
+                (skill_name, entry.get("description", ""))
+            )
+        category_descriptions = {
+            str(k): str(v)
+            for k, v in (snapshot.get("category_descriptions") or {}).items()
        }
-        if not _skill_should_show(conditions, available_tools, available_toolsets):
-            continue
-        skills_by_category.setdefault(category, []).append((skill_name, desc))
+    else:
+        # Cold path: full filesystem scan + write snapshot for next time
+        skill_entries: list[dict] = []
+        for skill_file in iter_skill_index_files(skills_dir, "SKILL.md"):
+            is_compatible, frontmatter, desc = _parse_skill_file(skill_file)
+            entry = _build_snapshot_entry(skill_file, skills_dir, frontmatter, desc)
+            skill_entries.append(entry)
+            if not is_compatible:
+                continue
+            skill_name = entry["skill_name"]
+            if entry["frontmatter_name"] in disabled or skill_name in disabled:
+                continue
+            if not _skill_should_show(
+                extract_skill_conditions(frontmatter),
+                available_tools,
+                available_toolsets,
+            ):
+                continue
+            skills_by_category.setdefault(entry["category"], []).append(
+                (skill_name, entry["description"])
+            )

-    if not skills_by_category:
-        return ""
-
-    # Read category-level descriptions from DESCRIPTION.md
-    # Checks both the exact category path and parent directories
-    category_descriptions = {}
-    for category in skills_by_category:
-        cat_path = Path(category)
-        desc_file = skills_dir / cat_path / "DESCRIPTION.md"
-        if desc_file.exists():
+        # Read category-level DESCRIPTION.md files
+        for desc_file in iter_skill_index_files(skills_dir, "DESCRIPTION.md"):
            try:
                content = desc_file.read_text(encoding="utf-8")
-                match = re.search(r"^---\s*\n.*?description:\s*(.+?)\s*\n.*?^---", content, re.MULTILINE | re.DOTALL)
-                if match:
-                    category_descriptions[category] = match.group(1).strip()
+                fm, _ = parse_frontmatter(content)
+                cat_desc = fm.get("description")
+                if not cat_desc:
+                    continue
+                rel = desc_file.relative_to(skills_dir)
+                cat = "/".join(rel.parts[:-1]) if len(rel.parts) > 1 else "general"
+                category_descriptions[cat] = str(cat_desc).strip().strip("'\"")
            except Exception as e:
                logger.debug("Could not read skill description %s: %s", desc_file, e)

-    index_lines = []
-    for category in sorted(skills_by_category.keys()):
-        cat_desc = category_descriptions.get(category, "")
-        if cat_desc:
-            index_lines.append(f"  {category}: {cat_desc}")
-        else:
-            index_lines.append(f"  {category}:")
-        # Deduplicate and sort skills within each category
-        seen = set()
-        for name, desc in sorted(skills_by_category[category], key=lambda x: x[0]):
-            if name in seen:
-                continue
-            seen.add(name)
-            if desc:
-                index_lines.append(f"    - {name}: {desc}")
-            else:
-                index_lines.append(f"    - {name}")
+        _write_skills_snapshot(
+            skills_dir,
+            _build_skills_manifest(skills_dir),
+            skill_entries,
+            category_descriptions,
+        )

-    return (
-        "## Skills (mandatory)\n"
-        "Before replying, scan the skills below. If one clearly matches your task, "
-        "load it with skill_view(name) and follow its instructions. "
-        "If a skill has issues, fix it with skill_manage(action='patch').\n"
-        "After difficult/iterative tasks, offer to save as a skill. "
-        "If a skill you loaded was missing steps, had wrong commands, or needed "
-        "pitfalls you discovered, update it before finishing.\n"
-        "\n"
-        "<available_skills>\n"
-        + "\n".join(index_lines) + "\n"
-        "</available_skills>\n"
-        "\n"
-        "If none match, proceed normally without loading a skill."
-    )
+    if not skills_by_category:
+        result = ""
+    else:
+        index_lines = []
+        for category in sorted(skills_by_category.keys()):
+            cat_desc = category_descriptions.get(category, "")
+            if cat_desc:
+                index_lines.append(f"  {category}: {cat_desc}")
+            else:
+                index_lines.append(f"  {category}:")
+            # Deduplicate and sort skills within each category
+            seen = set()
+            for name, desc in sorted(skills_by_category[category], key=lambda x: x[0]):
+                if name in seen:
+                    continue
+                seen.add(name)
+                if desc:
+                    index_lines.append(f"    - {name}: {desc}")
+                else:
+                    index_lines.append(f"    - {name}")
+
+        result = (
+            "## Skills (mandatory)\n"
+            "Before replying, scan the skills below. If one clearly matches your task, "
+            "load it with skill_view(name) and follow its instructions. "
+            "If a skill has issues, fix it with skill_manage(action='patch').\n"
+            "After difficult/iterative tasks, offer to save as a skill. "
+            "If a skill you loaded was missing steps, had wrong commands, or needed "
+            "pitfalls you discovered, update it before finishing.\n"
+            "\n"
+            "<available_skills>\n"
+            + "\n".join(index_lines) + "\n"
+            "</available_skills>\n"
+            "\n"
+            "If none match, proceed normally without loading a skill."
+        )
+
+    # ── Store in LRU cache ────────────────────────────────────────────
+    with _SKILLS_PROMPT_CACHE_LOCK:
+        _SKILLS_PROMPT_CACHE[cache_key] = result
+        _SKILLS_PROMPT_CACHE.move_to_end(cache_key)
+        while len(_SKILLS_PROMPT_CACHE) > _SKILLS_PROMPT_CACHE_MAX:
+            _SKILLS_PROMPT_CACHE.popitem(last=False)
+
+    return result


 # =========================================================================
@@ -0,0 +1,203 @@
+"""Lightweight skill metadata utilities shared by prompt_builder and skills_tool.
+
+This module intentionally avoids importing the tool registry, CLI config, or any
+heavy dependency chain.  It is safe to import at module level without triggering
+tool registration or provider resolution.
+"""
+
+import logging
+import os
+import re
+import sys
+from pathlib import Path
+from typing import Any, Dict, List, Optional, Set, Tuple
+
+from hermes_constants import get_hermes_home
+
+logger = logging.getLogger(__name__)
+
+# ── Platform mapping ──────────────────────────────────────────────────────
+
+PLATFORM_MAP = {
+    "macos": "darwin",
+    "linux": "linux",
+    "windows": "win32",
+}
+
+EXCLUDED_SKILL_DIRS = frozenset((".git", ".github", ".hub"))
+
+# ── Lazy YAML loader ─────────────────────────────────────────────────────
+
+_yaml_load_fn = None
+
+
+def yaml_load(content: str):
+    """Parse YAML with lazy import and CSafeLoader preference."""
+    global _yaml_load_fn
+    if _yaml_load_fn is None:
+        import yaml
+
+        loader = getattr(yaml, "CSafeLoader", None) or yaml.SafeLoader
+
+        def _load(value: str):
+            return yaml.load(value, Loader=loader)
+
+        _yaml_load_fn = _load
+    return _yaml_load_fn(content)
+
+
+# ── Frontmatter parsing ──────────────────────────────────────────────────
+
+
+def parse_frontmatter(content: str) -> Tuple[Dict[str, Any], str]:
+    """Parse YAML frontmatter from a markdown string.
+
+    Uses yaml with CSafeLoader for full YAML support (nested metadata, lists)
+    with a fallback to simple key:value splitting for robustness.
+
+    Returns:
+        (frontmatter_dict, remaining_body)
+    """
+    frontmatter: Dict[str, Any] = {}
+    body = content
+
+    if not content.startswith("---"):
+        return frontmatter, body
+
+    end_match = re.search(r"\n---\s*\n", content[3:])
+    if not end_match:
+        return frontmatter, body
+
+    yaml_content = content[3 : end_match.start() + 3]
+    body = content[end_match.end() + 3 :]
+
+    try:
+        parsed = yaml_load(yaml_content)
+        if isinstance(parsed, dict):
+            frontmatter = parsed
+    except Exception:
+        # Fallback: simple key:value parsing for malformed YAML
+        for line in yaml_content.strip().split("\n"):
+            if ":" not in line:
+                continue
+            key, value = line.split(":", 1)
+            frontmatter[key.strip()] = value.strip()
+
+    return frontmatter, body
+
+
+# ── Platform matching ─────────────────────────────────────────────────────
+
+
+def skill_matches_platform(frontmatter: Dict[str, Any]) -> bool:
+    """Return True when the skill is compatible with the current OS.
+
+    Skills declare platform requirements via a top-level ``platforms`` list
+    in their YAML frontmatter::
+
+        platforms: [macos]          # macOS only
+        platforms: [macos, linux]   # macOS and Linux
+
+    If the field is absent or empty the skill is compatible with **all**
+    platforms (backward-compatible default).
+    """
+    platforms = frontmatter.get("platforms")
+    if not platforms:
+        return True
+    if not isinstance(platforms, list):
+        platforms = [platforms]
+    current = sys.platform
+    for platform in platforms:
+        normalized = str(platform).lower().strip()
+        mapped = PLATFORM_MAP.get(normalized, normalized)
+        if current.startswith(mapped):
+            return True
+    return False
+
+
+# ── Disabled skills ───────────────────────────────────────────────────────
+
+
+def get_disabled_skill_names() -> Set[str]:
+    """Read disabled skill names from config.yaml.
+
+    Resolves platform from ``HERMES_PLATFORM`` env var, falls back to
+    the global disabled list.  Reads the config file directly (no CLI
+    config imports) to stay lightweight.
+    """
+    config_path = get_hermes_home() / "config.yaml"
+    if not config_path.exists():
+        return set()
+    try:
+        parsed = yaml_load(config_path.read_text(encoding="utf-8"))
+    except Exception as e:
+        logger.debug("Could not read skill config %s: %s", config_path, e)
+        return set()
+    if not isinstance(parsed, dict):
+        return set()
+
+    skills_cfg = parsed.get("skills")
+    if not isinstance(skills_cfg, dict):
+        return set()
+
+    resolved_platform = os.getenv("HERMES_PLATFORM")
+    if resolved_platform:
+        platform_disabled = (skills_cfg.get("platform_disabled") or {}).get(
+            resolved_platform
+        )
+        if platform_disabled is not None:
+            return _normalize_string_set(platform_disabled)
+    return _normalize_string_set(skills_cfg.get("disabled"))
+
+
+def _normalize_string_set(values) -> Set[str]:
+    if values is None:
+        return set()
+    if isinstance(values, str):
+        values = [values]
+    return {str(v).strip() for v in values if str(v).strip()}
+
+
+# ── Condition extraction ──────────────────────────────────────────────────
+
+
+def extract_skill_conditions(frontmatter: Dict[str, Any]) -> Dict[str, List]:
+    """Extract conditional activation fields from parsed frontmatter."""
+    hermes = (frontmatter.get("metadata") or {}).get("hermes") or {}
+    return {
+        "fallback_for_toolsets": hermes.get("fallback_for_toolsets", []),
+        "requires_toolsets": hermes.get("requires_toolsets", []),
+        "fallback_for_tools": hermes.get("fallback_for_tools", []),
+        "requires_tools": hermes.get("requires_tools", []),
+    }
+
+
+# ── Description extraction ────────────────────────────────────────────────
+
+
+def extract_skill_description(frontmatter: Dict[str, Any]) -> str:
+    """Extract a truncated description from parsed frontmatter."""
+    raw_desc = frontmatter.get("description", "")
+    if not raw_desc:
+        return ""
+    desc = str(raw_desc).strip().strip("'\"")
+    if len(desc) > 60:
+        return desc[:57] + "..."
+    return desc
+
+
+# ── File iteration ────────────────────────────────────────────────────────
+
+
+def iter_skill_index_files(skills_dir: Path, filename: str):
+    """Walk skills_dir yielding sorted paths matching *filename*.
+
+    Excludes ``.git``, ``.github``, ``.hub`` directories.
+    """
+    matches = []
+    for root, dirs, files in os.walk(skills_dir):
+        dirs[:] = [d for d in dirs if d not in EXCLUDED_SKILL_DIRS]
+        if filename in files:
+            matches.append(Path(root) / filename)
+    for path in sorted(matches, key=lambda p: str(p.relative_to(skills_dir))):
+        yield path
@@ -19,7 +19,7 @@ _TITLE_PROMPT = (
 )


-def generate_title(user_message: str, assistant_response: str, timeout: float = 15.0) -> Optional[str]:
+def generate_title(user_message: str, assistant_response: str, timeout: float = 30.0) -> Optional[str]:
    """Generate a session title from the first exchange.

    Uses the auxiliary LLM client (cheapest/fastest available model).
@@ -7,6 +7,7 @@
 # =============================================================================
 model:
  # Default model to use (can be overridden with --model flag)
+  # Both "default" and "model" work as the key name here.
  default: "anthropic/claude-opus-4.6"
  
  # Inference provider selection:
@@ -688,6 +689,12 @@ display:
  # Toggle at runtime with /verbose in the CLI
  tool_progress: all

+  # What Enter does when Hermes is already busy in the CLI.
+  #   interrupt: Interrupt the current run and redirect Hermes (default)
+  #   queue:     Queue your message for the next turn
+  # Ctrl+C always interrupts regardless of this setting.
+  busy_input_mode: interrupt
+
  # Background process notifications (gateway/messaging only).
  # Controls how chatty the process watcher is when you use
  # terminal(background=true, check_interval=...) from Telegram/Discord/etc.
@@ -205,6 +205,7 @@ def load_cli_config() -> Dict[str, Any]:
            "resume_display": "full",
            "show_reasoning": False,
            "streaming": True,
+            "busy_input_mode": "interrupt",

            "skin": "default",
        },
@@ -448,6 +449,17 @@ try:
 except Exception:
    pass  # Skin engine is optional — default skin used if unavailable

+# Neuter AsyncHttpxClientWrapper.__del__ before any AsyncOpenAI clients are
+# created.  The SDK's __del__ schedules aclose() on asyncio.get_running_loop()
+# which, during CLI idle time, finds prompt_toolkit's event loop and tries to
+# close TCP transports bound to dead worker loops — producing
+# "Event loop is closed" / "Press ENTER to continue..." errors.
+try:
+    from agent.auxiliary_client import neuter_async_httpx_del
+    neuter_async_httpx_del()
+except Exception:
+    pass
+
 from rich import box as rich_box
 from rich.console import Console
 from rich.markup import escape as _escape
@@ -1035,13 +1047,18 @@ class HermesCLI:
        self.config = CLI_CONFIG
        self.compact = compact if compact is not None else CLI_CONFIG["display"].get("compact", False)
        # tool_progress: "off", "new", "all", "verbose" (from config.yaml display section)
-        self.tool_progress_mode = CLI_CONFIG["display"].get("tool_progress", "all")
+        # YAML 1.1 parses bare `off` as boolean False — normalise to string.
+        _raw_tp = CLI_CONFIG["display"].get("tool_progress", "all")
+        self.tool_progress_mode = "off" if _raw_tp is False else str(_raw_tp)
        # resume_display: "full" (show history) | "minimal" (one-liner only)
        self.resume_display = CLI_CONFIG["display"].get("resume_display", "full")
        # bell_on_complete: play terminal bell (\a) when agent finishes a response
        self.bell_on_complete = CLI_CONFIG["display"].get("bell_on_complete", False)
        # show_reasoning: display model thinking/reasoning before the response
        self.show_reasoning = CLI_CONFIG["display"].get("show_reasoning", False)
+        # busy_input_mode: "interrupt" (Enter interrupts current run) or "queue" (Enter queues for next turn)
+        _bim = CLI_CONFIG["display"].get("busy_input_mode", "interrupt")
+        self.busy_input_mode = "queue" if str(_bim).strip().lower() == "queue" else "interrupt"

        self.verbose = verbose if verbose is not None else (self.tool_progress_mode == "verbose")
        
@@ -1061,12 +1078,12 @@ class HermesCLI:
        # authoritative.  This avoids conflicts in multi-agent setups where
        # env vars would stomp each other.
        _model_config = CLI_CONFIG.get("model", {})
-        _config_model = _model_config.get("default", "") if isinstance(_model_config, dict) else (_model_config or "")
+        _config_model = (_model_config.get("default") or _model_config.get("model") or "") if isinstance(_model_config, dict) else (_model_config or "")
        _FALLBACK_MODEL = "anthropic/claude-opus-4.6"
        self.model = model or _config_model or _FALLBACK_MODEL
        # Auto-detect model from local server if still on fallback
        if self.model == _FALLBACK_MODEL:
-            _base_url = _model_config.get("base_url", "") if isinstance(_model_config, dict) else ""
+            _base_url = (_model_config.get("base_url") or "") if isinstance(_model_config, dict) else ""
            if "localhost" in _base_url or "127.0.0.1" in _base_url:
                from hermes_cli.runtime_provider import _auto_detect_local_model
                _detected = _auto_detect_local_model(_base_url)
@@ -1329,7 +1346,12 @@ class HermesCLI:
    def _build_status_bar_text(self, width: Optional[int] = None) -> str:
        try:
            snapshot = self._get_status_bar_snapshot()
-            width = width or shutil.get_terminal_size((80, 24)).columns
+            if width is None:
+                try:
+                    from prompt_toolkit.application import get_app
+                    width = get_app().output.get_size().columns
+                except Exception:
+                    width = shutil.get_terminal_size((80, 24)).columns
            percent = snapshot["context_percent"]
            percent_label = f"{percent}%" if percent is not None else "--"
            duration_label = snapshot["duration"]
@@ -1359,7 +1381,16 @@ class HermesCLI:
            return []
        try:
            snapshot = self._get_status_bar_snapshot()
-            width = shutil.get_terminal_size((80, 24)).columns
+            # Use prompt_toolkit's own terminal width when running inside the
+            # TUI — shutil.get_terminal_size() can return stale or fallback
+            # values (especially on SSH) that differ from what prompt_toolkit
+            # actually renders, causing the fragments to overflow to a second
+            # line and produce duplicated status bar rows over long sessions.
+            try:
+                from prompt_toolkit.application import get_app
+                width = get_app().output.get_size().columns
+            except Exception:
+                width = shutil.get_terminal_size((80, 24)).columns
            duration_label = snapshot["duration"]

            if width < 52:
@@ -1594,6 +1625,7 @@ class HermesCLI:
        if not text:
            return
        self._reasoning_stream_started = True
+        self._reasoning_shown_this_turn = True
        if getattr(self, "_stream_box_opened", False):
            return

@@ -2929,6 +2961,82 @@ class HermesCLI:
        if not silent:
            print("(^_^)v New session started!")

+    def _handle_resume_command(self, cmd_original: str) -> None:
+        """Handle /resume <session_id_or_title> — switch to a previous session mid-conversation."""
+        parts = cmd_original.split(None, 1)
+        target = parts[1].strip() if len(parts) > 1 else ""
+
+        if not target:
+            _cprint("  Usage: /resume <session_id_or_title>")
+            _cprint("  Tip:   Use /history or `hermes sessions list` to find sessions.")
+            return
+
+        if not self._session_db:
+            _cprint("  Session database not available.")
+            return
+
+        # Resolve title or ID
+        from hermes_cli.main import _resolve_session_by_name_or_id
+        resolved = _resolve_session_by_name_or_id(target)
+        target_id = resolved or target
+
+        session_meta = self._session_db.get_session(target_id)
+        if not session_meta:
+            _cprint(f"  Session not found: {target}")
+            _cprint("  Use /history or `hermes sessions list` to see available sessions.")
+            return
+
+        if target_id == self.session_id:
+            _cprint("  Already on that session.")
+            return
+
+        # End current session
+        try:
+            self._session_db.end_session(self.session_id, "resumed_other")
+        except Exception:
+            pass
+
+        # Switch to the target session
+        self.session_id = target_id
+        self._resumed = True
+        self._pending_title = None
+
+        # Load conversation history
+        restored = self._session_db.get_messages_as_conversation(target_id)
+        self.conversation_history = restored or []
+
+        # Re-open the target session so it's not marked as ended
+        try:
+            self._session_db.reopen_session(target_id)
+        except Exception:
+            pass
+
+        # Sync the agent if already initialised
+        if self.agent:
+            self.agent.session_id = target_id
+            self.agent.reset_session_state()
+            if hasattr(self.agent, "_last_flushed_db_idx"):
+                self.agent._last_flushed_db_idx = len(self.conversation_history)
+            if hasattr(self.agent, "_todo_store"):
+                try:
+                    from tools.todo_tool import TodoStore
+                    self.agent._todo_store = TodoStore()
+                except Exception:
+                    pass
+            if hasattr(self.agent, "_invalidate_system_prompt"):
+                self.agent._invalidate_system_prompt()
+
+        title_part = f" \"{session_meta['title']}\"" if session_meta.get("title") else ""
+        msg_count = len([m for m in self.conversation_history if m.get("role") == "user"])
+        if self.conversation_history:
+            _cprint(
+                f"  ↻ Resumed session {target_id}{title_part}"
+                f" ({msg_count} user message{'s' if msg_count != 1 else ''},"
+                f" {len(self.conversation_history)} total)"
+            )
+        else:
+            _cprint(f"  ↻ Resumed session {target_id}{title_part} — no messages, starting fresh.")
+
    def reset_conversation(self):
        """Reset the conversation by starting a new session."""
        self.new_session()
@@ -3647,6 +3755,8 @@ class HermesCLI:
                    _cprint("  Session database not available.")
        elif canonical == "new":
            self.new_session()
+        elif canonical == "resume":
+            self._handle_resume_command(cmd_original)
        elif canonical == "provider":
            self._show_model_and_providers()
        elif canonical == "prompt":
@@ -3722,17 +3832,17 @@ class HermesCLI:
        elif canonical == "background":
            self._handle_background_command(cmd_original)
        elif canonical == "queue":
-            if not self._agent_running:
-                _cprint("  /queue only works while Hermes is busy. Just type your message normally.")
+            # Extract prompt after "/queue " or "/q "
+            parts = cmd_original.split(None, 1)
+            payload = parts[1].strip() if len(parts) > 1 else ""
+            if not payload:
+                _cprint("  Usage: /queue <prompt>")
            else:
-                # Extract prompt after "/queue " or "/q "
-                parts = cmd_original.split(None, 1)
-                payload = parts[1].strip() if len(parts) > 1 else ""
-                if not payload:
-                    _cprint("  Usage: /queue <prompt>")
-                else:
-                    self._pending_input.put(payload)
+                self._pending_input.put(payload)
+                if self._agent_running:
                    _cprint(f"  Queued for the next turn: {payload[:80]}{'...' if len(payload) > 80 else ''}")
+                else:
+                    _cprint(f"  Queued: {payload[:80]}{'...' if len(payload) > 80 else ''}")
        elif canonical == "skin":
            self._handle_skin_command(cmd_original)
        elif canonical == "voice":
@@ -3924,6 +4034,17 @@ class HermesCLI:
                    provider_data_collection=self._provider_data_collection,
                    fallback_model=self._fallback_model,
                )
+                # Silence raw spinner; route thinking through TUI widget when no foreground agent is active.
+                bg_agent._print_fn = lambda *_a, **_kw: None
+
+                def _bg_thinking(text: str) -> None:
+                    # Concurrent bg tasks may race on _spinner_text; acceptable for best-effort UI.
+                    if not self._agent_running:
+                        self._spinner_text = text
+                        if self._app:
+                            self._app.invalidate()
+
+                bg_agent.thinking_callback = _bg_thinking

                result = bg_agent.run_conversation(
                    user_message=prompt,
@@ -3986,6 +4107,9 @@ class HermesCLI:
                _cprint(f"  ❌ Background task #{task_num} failed: {e}")
            finally:
                self._background_tasks.pop(task_id, None)
+                # Clear spinner only if no foreground agent owns it
+                if not self._agent_running:
+                    self._spinner_text = ""
                if self._app:
                    self._invalidate(min_interval=0)

@@ -4396,7 +4520,7 @@ class HermesCLI:
        compressor = agent.context_compressor
        last_prompt = compressor.last_prompt_tokens
        ctx_len = compressor.context_length
-        pct = (last_prompt / ctx_len * 100) if ctx_len else 0
+        pct = min(100, (last_prompt / ctx_len * 100)) if ctx_len else 0
        compressions = compressor.compression_count

        msg_count = len(self.conversation_history)
@@ -5424,6 +5548,13 @@ class HermesCLI:
            except Exception as e:
                logging.debug("@ context reference expansion failed: %s", e)

+        # Sanitize surrogate characters that can arrive via clipboard paste from
+        # rich-text editors (Google Docs, Word, etc.).  Lone surrogates are invalid
+        # UTF-8 and crash JSON serialization in the OpenAI SDK.
+        if isinstance(message, str):
+            from run_agent import _sanitize_surrogates
+            message = _sanitize_surrogates(message)
+
        # Add user message to history
        self.conversation_history.append({"role": "user", "content": message})

@@ -5436,6 +5567,10 @@ class HermesCLI:

            # Reset streaming display state for this turn
            self._reset_stream_state()
+            # Separate from _reset_stream_state because this must persist
+            # across intermediate turn boundaries (tool-calling loops) — only
+            # reset at the start of each user turn.
+            self._reasoning_shown_this_turn = False

            # --- Streaming TTS setup ---
            # When ElevenLabs is the TTS provider and sounddevice is available,
@@ -5580,6 +5715,16 @@ class HermesCLI:

            agent_thread.join()  # Ensure agent thread completes

+            # Proactively clean up async clients whose event loop is dead.
+            # The agent thread may have created AsyncOpenAI clients bound
+            # to a per-thread event loop; if that loop is now closed, those
+            # clients' __del__ would crash prompt_toolkit's loop on GC.
+            try:
+                from agent.auxiliary_client import cleanup_stale_async_clients
+                cleanup_stale_async_clients()
+            except Exception:
+                pass
+
            # Flush any remaining streamed text and close the box
            self._flush_stream()

@@ -5640,8 +5785,13 @@ class HermesCLI:
            response_previewed = result.get("response_previewed", False) if result else False

            # Display reasoning (thinking) box if enabled and available.
-            # Skip when streaming already showed reasoning live.
-            if self.show_reasoning and result and not self._reasoning_stream_started:
+            # Skip when streaming already showed reasoning live.  Use the
+            # turn-persistent flag (_reasoning_shown_this_turn) instead of
+            # _reasoning_stream_started — the latter gets reset during
+            # intermediate turn boundaries (tool-calling loops), which caused
+            # the reasoning box to re-render after the final response.
+            _reasoning_already_shown = getattr(self, '_reasoning_shown_this_turn', False)
+            if self.show_reasoning and result and not _reasoning_already_shown:
                reasoning = result.get("last_reasoning")
                if reasoning:
                    w = shutil.get_terminal_size().columns
@@ -5762,10 +5912,22 @@ class HermesCLI:
            else:
                duration_str = f"{seconds}s"
            
+            # Look up session title for resume-by-name hint
+            session_title = None
+            if self._session_db:
+                try:
+                    session_title = self._session_db.get_session_title(self.session_id)
+                except Exception:
+                    pass
+
            print("Resume this session with:")
            print(f"  hermes --resume {self.session_id}")
+            if session_title:
+                print(f"  hermes -c \"{session_title}\"")
            print()
            print(f"Session:        {self.session_id}")
+            if session_title:
+                print(f"Title:          {session_title}")
            print(f"Duration:       {duration_str}")
            print(f"Messages:       {msg_count} ({user_msgs} user, {tool_calls} tool calls)")
        else:
@@ -5941,7 +6103,7 @@ class HermesCLI:
            from honcho_integration.client import HonchoClientConfig
            from agent.display import honcho_session_line, write_tty
            hcfg = HonchoClientConfig.from_global_config()
-            if hcfg.enabled and hcfg.api_key and hcfg.explicitly_configured:
+            if hcfg.enabled and (hcfg.api_key or hcfg.base_url) and hcfg.explicitly_configured:
                sname = hcfg.resolve_session_name(session_id=self.session_id)
                if sname:
                    write_tty(honcho_session_line(hcfg.workspace_id, sname) + "\n")
@@ -6028,10 +6190,18 @@ class HermesCLI:
        set_approval_callback(self._approval_callback)
        set_secret_capture_callback(self._secret_capture_callback)

-        # Ensure tirith security scanner is available (downloads if needed)
+        # Ensure tirith security scanner is available (downloads if needed).
+        # Warn the user if tirith is enabled in config but not available,
+        # so they know command security scanning is degraded.
        try:
            from tools.tirith_security import ensure_installed
-            ensure_installed(log_failures=False)
+            tirith_path = ensure_installed(log_failures=False)
+            if tirith_path is None:
+                security_cfg = self.config.get("security", {}) or {}
+                tirith_enabled = security_cfg.get("tirith_enabled", True)
+                if tirith_enabled:
+                    _cprint(f"  {_DIM}⚠ tirith security scanner enabled but not available "
+                            f"— command scanning will use pattern matching only{_RST}")
        except Exception:
            pass  # Non-fatal — fail-open at scan time if unavailable
        
@@ -6112,16 +6282,22 @@ class HermesCLI:
                # Bundle text + images as a tuple when images are present
                payload = (text, images) if images else text
                if self._agent_running and not (text and text.startswith("/")):
-                    self._interrupt_queue.put(payload)
-                    # Debug: log to file when message enters interrupt queue
-                    try:
-                        _dbg = _hermes_home / "interrupt_debug.log"
-                        with open(_dbg, "a") as _f:
-                            import time as _t
-                            _f.write(f"{_t.strftime('%H:%M:%S')} ENTER: queued interrupt msg={str(payload)[:60]!r}, "
-                                     f"agent_running={self._agent_running}\n")
-                    except Exception:
-                        pass
+                    if self.busy_input_mode == "queue":
+                        # Queue for the next turn instead of interrupting
+                        self._pending_input.put(payload)
+                        preview = text if text else f"[{len(images)} image{'s' if len(images) != 1 else ''} attached]"
+                        _cprint(f"  Queued for the next turn: {preview[:80]}{'...' if len(preview) > 80 else ''}")
+                    else:
+                        self._interrupt_queue.put(payload)
+                        # Debug: log to file when message enters interrupt queue
+                        try:
+                            _dbg = _hermes_home / "interrupt_debug.log"
+                            with open(_dbg, "a") as _f:
+                                import time as _t
+                                _f.write(f"{_t.strftime('%H:%M:%S')} ENTER: queued interrupt msg={str(payload)[:60]!r}, "
+                                         f"agent_running={self._agent_running}\n")
+                        except Exception:
+                            pass
                else:
                    self._pending_input.put(payload)
                event.app.current_buffer.reset(append_to_history=True)
@@ -6501,6 +6677,7 @@ class HermesCLI:
        # Paste collapsing: detect large pastes and save to temp file
        _paste_counter = [0]
        _prev_text_len = [0]
+        _prev_newline_count = [0]
        _paste_just_collapsed = [False]

        def _on_text_changed(buf):
@@ -6509,18 +6686,27 @@ class HermesCLI:
            When bracketed paste is available, handle_paste collapses
            large pastes directly.  This handler is a fallback for
            terminals without bracketed paste support.
+
+            Two heuristics (either triggers collapse):
+            1. Many characters added at once (chars_added > 1) — works
+               when the terminal delivers the paste in one event-loop tick.
+            2. Newline count jumped by 4+ in a single text-change event —
+               catches terminals that feed characters individually but
+               still batch newlines.  Alt+Enter only adds 1 newline per
+               event so it never triggers this.
            """
            text = buf.text
            chars_added = len(text) - _prev_text_len[0]
            _prev_text_len[0] = len(text)
            if _paste_just_collapsed[0]:
                _paste_just_collapsed[0] = False
+                _prev_newline_count[0] = text.count('\n')
                return
            line_count = text.count('\n')
-            # Heuristic: a real paste adds many characters at once (not just a
-            # single newline from Alt+Enter) AND the result has 5+ lines.
-            # Fallback for terminals without bracketed paste support.
-            if line_count >= 5 and chars_added > 1 and not text.startswith('/'):
+            newlines_added = line_count - _prev_newline_count[0]
+            _prev_newline_count[0] = line_count
+            is_paste = chars_added > 1 or newlines_added >= 4
+            if line_count >= 5 and is_paste and not text.startswith('/'):
                _paste_counter[0] += 1
                # Save to temp file
                paste_dir = _hermes_home / "pastes"
@@ -6528,6 +6714,7 @@ class HermesCLI:
                paste_file = paste_dir / f"paste_{_paste_counter[0]}_{datetime.now().strftime('%H%M%S')}.txt"
                paste_file.write_text(text, encoding="utf-8")
                # Replace buffer with compact reference
+                _paste_just_collapsed[0] = True
                buf.text = f"[Pasted text #{_paste_counter[0]}: {line_count + 1} lines \u2192 {paste_file}]"
                buf.cursor_position = len(buf.text)

@@ -6894,6 +7081,15 @@ class HermesCLI:
            Window(
                content=FormattedTextControl(lambda: cli_ref._get_status_bar_fragments()),
                height=1,
+                # Prevent fragments that overflow the terminal width from
+                # wrapping onto a second line, which causes the status bar to
+                # appear duplicated (one full + one partial row) during long
+                # sessions, especially on SSH where shutil.get_terminal_size
+                # may return stale values.  _get_status_bar_fragments now reads
+                # width from prompt_toolkit's own output object, so fragments
+                # will always fit; wrap_lines=False is the belt-and-suspenders
+                # guard against any future width mismatch.
+                wrap_lines=False,
            ),
            filter=Condition(lambda: cli_ref._status_bar_visible),
        )
@@ -7128,9 +7324,28 @@ class HermesCLI:
        # Register atexit cleanup so resources are freed even on unexpected exit
        atexit.register(_run_cleanup)
        
+        # Install a custom asyncio exception handler that suppresses the
+        # "Event loop is closed" RuntimeError from httpx transport cleanup.
+        # This is defense-in-depth — the primary fix is neuter_async_httpx_del
+        # which disables __del__ entirely, but older clients or SDK upgrades
+        # could bypass it.
+        def _suppress_closed_loop_errors(loop, context):
+            exc = context.get("exception")
+            if isinstance(exc, RuntimeError) and "Event loop is closed" in str(exc):
+                return  # silently suppress
+            # Fall back to default handler for everything else
+            loop.default_exception_handler(context)
+
        # Run the application with patch_stdout for proper output handling
        try:
            with patch_stdout():
+                # Set the custom handler on prompt_toolkit's event loop
+                try:
+                    import asyncio as _aio
+                    _loop = _aio.get_event_loop()
+                    _loop.set_exception_handler(_suppress_closed_loop_errors)
+                except Exception:
+                    pass
                app.run()
        except (EOFError, KeyboardInterrupt):
            pass
@@ -327,7 +327,20 @@ def load_jobs() -> List[Dict[str, Any]]:
        with open(JOBS_FILE, 'r', encoding='utf-8') as f:
            data = json.load(f)
            return data.get("jobs", [])
-    except (json.JSONDecodeError, IOError):
+    except json.JSONDecodeError:
+        # Retry with strict=False to handle bare control chars in string values
+        try:
+            with open(JOBS_FILE, 'r', encoding='utf-8') as f:
+                data = json.loads(f.read(), strict=False)
+                jobs = data.get("jobs", [])
+                if jobs:
+                    # Auto-repair: rewrite with proper escaping
+                    save_jobs(jobs)
+                    logger.warning("Auto-repaired jobs.json (had invalid control characters)")
+                return jobs
+        except Exception:
+            return []
+    except IOError:
        return []


@@ -598,6 +611,34 @@ def mark_job_run(job_id: str, success: bool, error: Optional[str] = None):
    save_jobs(jobs)


+def advance_next_run(job_id: str) -> bool:
+    """Preemptively advance next_run_at for a recurring job before execution.
+
+    Call this BEFORE run_job() so that if the process crashes mid-execution,
+    the job won't re-fire on the next gateway restart.  This converts the
+    scheduler from at-least-once to at-most-once for recurring jobs — missing
+    one run is far better than firing dozens of times in a crash loop.
+
+    One-shot jobs are left unchanged so they can still retry on restart.
+
+    Returns True if next_run_at was advanced, False otherwise.
+    """
+    jobs = load_jobs()
+    for job in jobs:
+        if job["id"] == job_id:
+            kind = job.get("schedule", {}).get("kind")
+            if kind not in ("cron", "interval"):
+                return False
+            now = _hermes_now().isoformat()
+            new_next = compute_next_run(job["schedule"], now)
+            if new_next and new_next != job.get("next_run_at"):
+                job["next_run_at"] = new_next
+                save_jobs(jobs)
+                return True
+            return False
+    return False
+
+
 def get_due_jobs() -> List[Dict[str, Any]]:
    """Get all jobs that are due to run now.

@@ -35,7 +35,7 @@ logger = logging.getLogger(__name__)
 # Add parent directory to path for imports
 sys.path.insert(0, str(Path(__file__).parent.parent))

-from cron.jobs import get_due_jobs, mark_job_run, save_job_output
+from cron.jobs import get_due_jobs, mark_job_run, save_job_output, advance_next_run

 # Sentinel: when a cron agent has nothing new to report, it can start its
 # response with this marker to suppress delivery.  Output is still saved
@@ -524,6 +524,12 @@ def tick(verbose: bool = True) -> int:
        executed = 0
        for job in due_jobs:
            try:
+                # For recurring jobs (cron/interval), advance next_run_at to the
+                # next future occurrence BEFORE execution.  This way, if the
+                # process crashes mid-run, the job won't re-fire on restart.
+                # One-shot jobs are left alone so they can retry on restart.
+                advance_next_run(job["id"])
+
                success, output, final_response, error = run_job(job)

                output_file = save_job_output(job["id"], output)
@@ -101,21 +101,11 @@ Available methods:

 ### Patches (`patches.py`)

-**Problem**: Some hermes-agent tools use `asyncio.run()` internally (e.g., the Modal backend via SWE-ReX). This crashes when called from inside Atropos's event loop because `asyncio.run()` cannot be nested.
+**Problem**: Some hermes-agent tools use `asyncio.run()` internally (e.g., the Modal backend). This crashes when called from inside Atropos's event loop because `asyncio.run()` cannot be nested.

-**Solution**: `patches.py` monkey-patches `SwerexModalEnvironment` to use a dedicated background thread (`_AsyncWorker`) with its own event loop. The calling code sees the same sync interface, but internally the async work happens on a separate thread that doesn't conflict with Atropos's loop.
+**Solution**: `ModalEnvironment` uses a dedicated `_AsyncWorker` background thread with its own event loop. The calling code sees a sync interface, but internally all async Modal SDK calls happen on the worker thread so they don't conflict with Atropos's loop. This is built directly into `tools/environments/modal.py` — no monkey-patching required.

-What gets patched:
- `SwerexModalEnvironment.__init__` -- creates Modal deployment on a background thread
- `SwerexModalEnvironment.execute` -- runs commands on the same background thread
- `SwerexModalEnvironment.stop` -- stops deployment on the background thread
-
-The patches are:
- **Idempotent** -- calling `apply_patches()` multiple times is safe
- **Transparent** -- same interface and behavior, only the internal async execution changes
- **Universal** -- works identically in normal CLI use (no running event loop)
-
-Applied automatically at import time by `hermes_base_env.py`.
+`patches.py` is now a no-op (kept for backward compatibility with imports).

 ### Tool Call Parsers (`tool_call_parsers/`)

@@ -601,6 +601,14 @@ def _apply_env_overrides(config: GatewayConfig) -> None:
            config.platforms[Platform.TELEGRAM] = PlatformConfig()
        config.platforms[Platform.TELEGRAM].reply_to_mode = telegram_reply_mode
    
+    telegram_fallback_ips = os.getenv("TELEGRAM_FALLBACK_IPS", "")
+    if telegram_fallback_ips:
+        if Platform.TELEGRAM not in config.platforms:
+            config.platforms[Platform.TELEGRAM] = PlatformConfig()
+        config.platforms[Platform.TELEGRAM].extra["fallback_ips"] = [
+            ip.strip() for ip in telegram_fallback_ips.split(",") if ip.strip()
+        ]
+
    telegram_home = os.getenv("TELEGRAM_HOME_CHANNEL")
    if telegram_home and Platform.TELEGRAM in config.platforms:
        config.platforms[Platform.TELEGRAM].home_channel = HomeChannel(
@@ -25,7 +25,7 @@ import time
 from pathlib import Path
 from typing import Optional

-from hermes_cli.config import get_hermes_home
+from hermes_constants import get_hermes_dir


 # Unambiguous alphabet -- excludes 0/O, 1/I to prevent confusion
@@ -41,7 +41,7 @@ LOCKOUT_SECONDS = 3600              # Lockout duration after too many failures
 MAX_PENDING_PER_PLATFORM = 3        # Max pending codes per platform
 MAX_FAILED_ATTEMPTS = 5             # Failed approvals before lockout

-PAIRING_DIR = get_hermes_home() / "pairing"
+PAIRING_DIR = get_hermes_dir("platforms/pairing", "pairing")


 def _secure_write(path: Path, data: str) -> None:
@@ -166,7 +166,7 @@ class ResponseStore:

 _CORS_HEADERS = {
    "Access-Control-Allow-Methods": "GET, POST, DELETE, OPTIONS",
-    "Access-Control-Allow-Headers": "Authorization, Content-Type",
+    "Access-Control-Allow-Headers": "Authorization, Content-Type, Idempotency-Key",
 }


@@ -223,6 +223,23 @@ if AIOHTTP_AVAILABLE:
 else:
    body_limit_middleware = None  # type: ignore[assignment]

+_SECURITY_HEADERS = {
+    "X-Content-Type-Options": "nosniff",
+    "Referrer-Policy": "no-referrer",
+}
+
+
+if AIOHTTP_AVAILABLE:
+    @web.middleware
+    async def security_headers_middleware(request, handler):
+        """Add security headers to all responses (including errors)."""
+        response = await handler(request)
+        for k, v in _SECURITY_HEADERS.items():
+            response.headers.setdefault(k, v)
+        return response
+else:
+    security_headers_middleware = None  # type: ignore[assignment]
+

 class _IdempotencyCache:
    """In-memory idempotency cache with TTL and basic LRU semantics."""
@@ -307,6 +324,7 @@ class APIServerAdapter(BasePlatformAdapter):
        if "*" in self._cors_origins:
            headers = dict(_CORS_HEADERS)
            headers["Access-Control-Allow-Origin"] = "*"
+            headers["Access-Control-Max-Age"] = "600"
            return headers

        if origin not in self._cors_origins:
@@ -315,6 +333,7 @@ class APIServerAdapter(BasePlatformAdapter):
        headers = dict(_CORS_HEADERS)
        headers["Access-Control-Allow-Origin"] = origin
        headers["Vary"] = "Origin"
+        headers["Access-Control-Max-Age"] = "600"
        return headers

    def _origin_allowed(self, origin: str) -> bool:
@@ -366,14 +385,20 @@ class APIServerAdapter(BasePlatformAdapter):
        Create an AIAgent instance using the gateway's runtime config.

        Uses _resolve_runtime_agent_kwargs() to pick up model, api_key,
-        base_url, etc. from config.yaml / env vars.
+        base_url, etc. from config.yaml / env vars.  Toolsets are resolved
+        from config.yaml platform_toolsets.api_server (same as all other
+        gateway platforms), falling back to the hermes-api-server default.
        """
        from run_agent import AIAgent
-        from gateway.run import _resolve_runtime_agent_kwargs, _resolve_gateway_model
+        from gateway.run import _resolve_runtime_agent_kwargs, _resolve_gateway_model, _load_gateway_config
+        from hermes_cli.tools_config import _get_platform_tools

        runtime_kwargs = _resolve_runtime_agent_kwargs()
        model = _resolve_gateway_model()

+        user_config = _load_gateway_config()
+        enabled_toolsets = sorted(_get_platform_tools(user_config, "api_server"))
+
        max_iterations = int(os.getenv("HERMES_MAX_ITERATIONS", "90"))

        agent = AIAgent(
@@ -383,7 +408,7 @@ class APIServerAdapter(BasePlatformAdapter):
            quiet_mode=True,
            verbose_logging=False,
            ephemeral_system_prompt=ephemeral_system_prompt or None,
-            enabled_toolsets=["hermes-api-server"],
+            enabled_toolsets=enabled_toolsets,
            session_id=session_id,
            platform="api_server",
            stream_delta_callback=stream_delta_callback,
@@ -489,17 +514,21 @@ class APIServerAdapter(BasePlatformAdapter):
                if delta is not None:
                    _stream_q.put(delta)

-            # Start agent in background
+            # Start agent in background.  agent_ref is a mutable container
+            # so the SSE writer can interrupt the agent on client disconnect.
+            agent_ref = [None]
            agent_task = asyncio.ensure_future(self._run_agent(
                user_message=user_message,
                conversation_history=history,
                ephemeral_system_prompt=system_prompt,
                session_id=session_id,
                stream_delta_callback=_on_delta,
+                agent_ref=agent_ref,
            ))

            return await self._write_sse_chat_completion(
-                request, completion_id, model_name, created, _stream_q, agent_task
+                request, completion_id, model_name, created, _stream_q,
+                agent_task, agent_ref,
            )

        # Non-streaming: run the agent (with optional Idempotency-Key)
@@ -562,80 +591,107 @@ class APIServerAdapter(BasePlatformAdapter):

    async def _write_sse_chat_completion(
        self, request: "web.Request", completion_id: str, model: str,
-        created: int, stream_q, agent_task,
+        created: int, stream_q, agent_task, agent_ref=None,
    ) -> "web.StreamResponse":
-        """Write real streaming SSE from agent's stream_delta_callback queue."""
+        """Write real streaming SSE from agent's stream_delta_callback queue.
+
+        If the client disconnects mid-stream (network drop, browser tab close),
+        the agent is interrupted via ``agent.interrupt()`` so it stops making
+        LLM API calls, and the asyncio task wrapper is cancelled.
+        """
        import queue as _q

-        response = web.StreamResponse(
-            status=200,
-            headers={"Content-Type": "text/event-stream", "Cache-Control": "no-cache"},
-        )
+        sse_headers = {"Content-Type": "text/event-stream", "Cache-Control": "no-cache"}
+        # CORS middleware can't inject headers into StreamResponse after
+        # prepare() flushes them, so resolve CORS headers up front.
+        origin = request.headers.get("Origin", "")
+        cors = self._cors_headers_for_origin(origin) if origin else None
+        if cors:
+            sse_headers.update(cors)
+        response = web.StreamResponse(status=200, headers=sse_headers)
        await response.prepare(request)

-        # Role chunk
-        role_chunk = {
-            "id": completion_id, "object": "chat.completion.chunk",
-            "created": created, "model": model,
-            "choices": [{"index": 0, "delta": {"role": "assistant"}, "finish_reason": None}],
-        }
-        await response.write(f"data: {json.dumps(role_chunk)}\n\n".encode())
-
-        # Stream content chunks as they arrive from the agent
-        loop = asyncio.get_event_loop()
-        while True:
-            try:
-                delta = await loop.run_in_executor(None, lambda: stream_q.get(timeout=0.5))
-            except _q.Empty:
-                if agent_task.done():
-                    # Drain any remaining items
-                    while True:
-                        try:
-                            delta = stream_q.get_nowait()
-                            if delta is None:
-                                break
-                            content_chunk = {
-                                "id": completion_id, "object": "chat.completion.chunk",
-                                "created": created, "model": model,
-                                "choices": [{"index": 0, "delta": {"content": delta}, "finish_reason": None}],
-                            }
-                            await response.write(f"data: {json.dumps(content_chunk)}\n\n".encode())
-                        except _q.Empty:
-                            break
-                    break
-                continue
-
-            if delta is None:  # End of stream sentinel
-                break
-
-            content_chunk = {
+        try:
+            # Role chunk
+            role_chunk = {
                "id": completion_id, "object": "chat.completion.chunk",
                "created": created, "model": model,
-                "choices": [{"index": 0, "delta": {"content": delta}, "finish_reason": None}],
+                "choices": [{"index": 0, "delta": {"role": "assistant"}, "finish_reason": None}],
            }
-            await response.write(f"data: {json.dumps(content_chunk)}\n\n".encode())
+            await response.write(f"data: {json.dumps(role_chunk)}\n\n".encode())

-        # Get usage from completed agent
-        usage = {"input_tokens": 0, "output_tokens": 0, "total_tokens": 0}
-        try:
-            result, agent_usage = await agent_task
-            usage = agent_usage or usage
-        except Exception:
-            pass
+            # Stream content chunks as they arrive from the agent
+            loop = asyncio.get_event_loop()
+            while True:
+                try:
+                    delta = await loop.run_in_executor(None, lambda: stream_q.get(timeout=0.5))
+                except _q.Empty:
+                    if agent_task.done():
+                        # Drain any remaining items
+                        while True:
+                            try:
+                                delta = stream_q.get_nowait()
+                                if delta is None:
+                                    break
+                                content_chunk = {
+                                    "id": completion_id, "object": "chat.completion.chunk",
+                                    "created": created, "model": model,
+                                    "choices": [{"index": 0, "delta": {"content": delta}, "finish_reason": None}],
+                                }
+                                await response.write(f"data: {json.dumps(content_chunk)}\n\n".encode())
+                            except _q.Empty:
+                                break
+                        break
+                    continue

-        # Finish chunk
-        finish_chunk = {
-            "id": completion_id, "object": "chat.completion.chunk",
-            "created": created, "model": model,
-            "choices": [{"index": 0, "delta": {}, "finish_reason": "stop"}],
-            "usage": {
-                "prompt_tokens": usage.get("input_tokens", 0),
-                "completion_tokens": usage.get("output_tokens", 0),
-                "total_tokens": usage.get("total_tokens", 0),
-            },
-        }
-        await response.write(f"data: {json.dumps(finish_chunk)}\n\n".encode())
-        await response.write(b"data: [DONE]\n\n")
+                if delta is None:  # End of stream sentinel
+                    break
+
+                content_chunk = {
+                    "id": completion_id, "object": "chat.completion.chunk",
+                    "created": created, "model": model,
+                    "choices": [{"index": 0, "delta": {"content": delta}, "finish_reason": None}],
+                }
+                await response.write(f"data: {json.dumps(content_chunk)}\n\n".encode())
+
+            # Get usage from completed agent
+            usage = {"input_tokens": 0, "output_tokens": 0, "total_tokens": 0}
+            try:
+                result, agent_usage = await agent_task
+                usage = agent_usage or usage
+            except Exception:
+                pass
+
+            # Finish chunk
+            finish_chunk = {
+                "id": completion_id, "object": "chat.completion.chunk",
+                "created": created, "model": model,
+                "choices": [{"index": 0, "delta": {}, "finish_reason": "stop"}],
+                "usage": {
+                    "prompt_tokens": usage.get("input_tokens", 0),
+                    "completion_tokens": usage.get("output_tokens", 0),
+                    "total_tokens": usage.get("total_tokens", 0),
+                },
+            }
+            await response.write(f"data: {json.dumps(finish_chunk)}\n\n".encode())
+            await response.write(b"data: [DONE]\n\n")
+        except (ConnectionResetError, ConnectionAbortedError, BrokenPipeError, OSError):
+            # Client disconnected mid-stream.  Interrupt the agent so it
+            # stops making LLM API calls at the next loop iteration, then
+            # cancel the asyncio task wrapper.
+            agent = agent_ref[0] if agent_ref else None
+            if agent is not None:
+                try:
+                    agent.interrupt("SSE client disconnected")
+                except Exception:
+                    pass
+            if not agent_task.done():
+                agent_task.cancel()
+                try:
+                    await agent_task
+                except (asyncio.CancelledError, Exception):
+                    pass
+            logger.info("SSE client disconnected; interrupted agent task %s", completion_id)

        return response

@@ -1138,12 +1194,18 @@ class APIServerAdapter(BasePlatformAdapter):
        ephemeral_system_prompt: Optional[str] = None,
        session_id: Optional[str] = None,
        stream_delta_callback=None,
+        agent_ref: Optional[list] = None,
    ) -> tuple:
        """
        Create an agent and run a conversation in a thread executor.

        Returns ``(result_dict, usage_dict)`` where *usage_dict* contains
        ``input_tokens``, ``output_tokens`` and ``total_tokens``.
+
+        If *agent_ref* is a one-element list, the AIAgent instance is stored
+        at ``agent_ref[0]`` before ``run_conversation`` begins.  This allows
+        callers (e.g. the SSE writer) to call ``agent.interrupt()`` from
+        another thread to stop in-progress LLM calls.
        """
        loop = asyncio.get_event_loop()

@@ -1153,6 +1215,8 @@ class APIServerAdapter(BasePlatformAdapter):
                session_id=session_id,
                stream_delta_callback=stream_delta_callback,
            )
+            if agent_ref is not None:
+                agent_ref[0] = agent
            result = agent.run_conversation(
                user_message=user_message,
                conversation_history=conversation_history,
@@ -1177,10 +1241,11 @@ class APIServerAdapter(BasePlatformAdapter):
            return False

        try:
-            mws = [mw for mw in (cors_middleware, body_limit_middleware) if mw is not None]
+            mws = [mw for mw in (cors_middleware, body_limit_middleware, security_headers_middleware) if mw is not None]
            self._app = web.Application(middlewares=mws)
            self._app["api_server_adapter"] = self
            self._app.router.add_get("/health", self._handle_health)
+            self._app.router.add_get("/v1/health", self._handle_health)
            self._app.router.add_get("/v1/models", self._handle_models)
            self._app.router.add_post("/v1/chat/completions", self._handle_chat_completions)
            self._app.router.add_post("/v1/responses", self._handle_responses)
@@ -8,6 +8,7 @@ and implement the required methods.
 import asyncio
 import logging
 import os
+import random
 import re
 import uuid
 from abc import ABC, abstractmethod
@@ -26,6 +27,7 @@ sys.path.insert(0, str(_Path(__file__).resolve().parents[2]))
 from gateway.config import Platform, PlatformConfig
 from gateway.session import SessionSource, build_session_key
 from hermes_cli.config import get_hermes_home
+from hermes_constants import get_hermes_dir


 GATEWAY_SECRET_CAPTURE_UNSUPPORTED_MESSAGE = (
@@ -43,8 +45,8 @@ GATEWAY_SECRET_CAPTURE_UNSUPPORTED_MESSAGE = (
 # (e.g. Telegram file URLs expire after ~1 hour).
 # ---------------------------------------------------------------------------

-# Default location: {HERMES_HOME}/image_cache/
-IMAGE_CACHE_DIR = get_hermes_home() / "image_cache"
+# Default location: {HERMES_HOME}/cache/images/ (legacy: image_cache/)
+IMAGE_CACHE_DIR = get_hermes_dir("cache/images", "image_cache")


 def get_image_cache_dir() -> Path:
@@ -71,31 +73,51 @@ def cache_image_from_bytes(data: bytes, ext: str = ".jpg") -> str:
    return str(filepath)


-async def cache_image_from_url(url: str, ext: str = ".jpg") -> str:
+async def cache_image_from_url(url: str, ext: str = ".jpg", retries: int = 2) -> str:
    """
    Download an image from a URL and save it to the local cache.

-    Uses httpx for async download with a reasonable timeout.
+    Retries on transient failures (timeouts, 429, 5xx) with exponential
+    backoff so a single slow CDN response doesn't lose the media.

    Args:
        url: The HTTP/HTTPS URL to download from.
        ext: File extension including the dot (e.g. ".jpg", ".png").
+        retries: Number of retry attempts on transient failures.

    Returns:
        Absolute path to the cached image file as a string.
    """
+    import asyncio
    import httpx
+    import logging as _logging
+    _log = _logging.getLogger(__name__)

+    last_exc = None
    async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
-        response = await client.get(
-            url,
-            headers={
-                "User-Agent": "Mozilla/5.0 (compatible; HermesAgent/1.0)",
-                "Accept": "image/*,*/*;q=0.8",
-            },
-        )
-        response.raise_for_status()
-        return cache_image_from_bytes(response.content, ext)
+        for attempt in range(retries + 1):
+            try:
+                response = await client.get(
+                    url,
+                    headers={
+                        "User-Agent": "Mozilla/5.0 (compatible; HermesAgent/1.0)",
+                        "Accept": "image/*,*/*;q=0.8",
+                    },
+                )
+                response.raise_for_status()
+                return cache_image_from_bytes(response.content, ext)
+            except (httpx.TimeoutException, httpx.HTTPStatusError) as exc:
+                last_exc = exc
+                if isinstance(exc, httpx.HTTPStatusError) and exc.response.status_code < 429:
+                    raise
+                if attempt < retries:
+                    wait = 1.5 * (attempt + 1)
+                    _log.debug("Media cache retry %d/%d for %s (%.1fs): %s",
+                               attempt + 1, retries, url[:80], wait, exc)
+                    await asyncio.sleep(wait)
+                    continue
+                raise
+    raise last_exc


 def cleanup_image_cache(max_age_hours: int = 24) -> int:
@@ -126,7 +148,7 @@ def cleanup_image_cache(max_age_hours: int = 24) -> int:
 # here so the STT tool (OpenAI Whisper) can transcribe them from local files.
 # ---------------------------------------------------------------------------

-AUDIO_CACHE_DIR = get_hermes_home() / "audio_cache"
+AUDIO_CACHE_DIR = get_hermes_dir("cache/audio", "audio_cache")


 def get_audio_cache_dir() -> Path:
@@ -153,29 +175,51 @@ def cache_audio_from_bytes(data: bytes, ext: str = ".ogg") -> str:
    return str(filepath)


-async def cache_audio_from_url(url: str, ext: str = ".ogg") -> str:
+async def cache_audio_from_url(url: str, ext: str = ".ogg", retries: int = 2) -> str:
    """
    Download an audio file from a URL and save it to the local cache.

+    Retries on transient failures (timeouts, 429, 5xx) with exponential
+    backoff so a single slow CDN response doesn't lose the media.
+
    Args:
        url: The HTTP/HTTPS URL to download from.
        ext: File extension including the dot (e.g. ".ogg", ".mp3").
+        retries: Number of retry attempts on transient failures.

    Returns:
        Absolute path to the cached audio file as a string.
    """
+    import asyncio
    import httpx
+    import logging as _logging
+    _log = _logging.getLogger(__name__)

+    last_exc = None
    async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
-        response = await client.get(
-            url,
-            headers={
-                "User-Agent": "Mozilla/5.0 (compatible; HermesAgent/1.0)",
-                "Accept": "audio/*,*/*;q=0.8",
-            },
-        )
-        response.raise_for_status()
-        return cache_audio_from_bytes(response.content, ext)
+        for attempt in range(retries + 1):
+            try:
+                response = await client.get(
+                    url,
+                    headers={
+                        "User-Agent": "Mozilla/5.0 (compatible; HermesAgent/1.0)",
+                        "Accept": "audio/*,*/*;q=0.8",
+                    },
+                )
+                response.raise_for_status()
+                return cache_audio_from_bytes(response.content, ext)
+            except (httpx.TimeoutException, httpx.HTTPStatusError) as exc:
+                last_exc = exc
+                if isinstance(exc, httpx.HTTPStatusError) and exc.response.status_code < 429:
+                    raise
+                if attempt < retries:
+                    wait = 1.5 * (attempt + 1)
+                    _log.debug("Audio cache retry %d/%d for %s (%.1fs): %s",
+                               attempt + 1, retries, url[:80], wait, exc)
+                    await asyncio.sleep(wait)
+                    continue
+                raise
+    raise last_exc


 # ---------------------------------------------------------------------------
@@ -185,7 +229,7 @@ async def cache_audio_from_url(url: str, ext: str = ".ogg") -> str:
 # here so the agent can reference them by local file path.
 # ---------------------------------------------------------------------------

-DOCUMENT_CACHE_DIR = get_hermes_home() / "document_cache"
+DOCUMENT_CACHE_DIR = get_hermes_dir("cache/documents", "document_cache")

 SUPPORTED_DOCUMENT_TYPES = {
    ".pdf": "application/pdf",
@@ -312,7 +356,10 @@ class MessageEvent:
            return None
        # Split on space and get first word, strip the /
        parts = self.text.split(maxsplit=1)
-        return parts[0][1:].lower() if parts else None
+        raw = parts[0][1:].lower() if parts else None
+        if raw and "@" in raw:
+            raw = raw.split("@", 1)[0]
+        return raw
    
    def get_command_args(self) -> str:
        """Get the arguments after a command."""
@@ -329,6 +376,24 @@ class SendResult:
    message_id: Optional[str] = None
    error: Optional[str] = None
    raw_response: Any = None
+    retryable: bool = False  # True for transient errors (network, timeout) — base will retry automatically
+
+
+# Error substrings that indicate a transient network failure worth retrying
+_RETRYABLE_ERROR_PATTERNS = (
+    "connecterror",
+    "connectionerror",
+    "connectionreset",
+    "connectionrefused",
+    "timeout",
+    "timed out",
+    "network",
+    "broken pipe",
+    "remotedisconnected",
+    "eoferror",
+    "readtimeout",
+    "writetimeout",
+)


 # Type for message handlers
@@ -833,6 +898,91 @@ class BasePlatformAdapter(ABC):
                except Exception:
                    pass
    
+    @staticmethod
+    def _is_retryable_error(error: Optional[str]) -> bool:
+        """Return True if the error string looks like a transient network failure."""
+        if not error:
+            return False
+        lowered = error.lower()
+        return any(pat in lowered for pat in _RETRYABLE_ERROR_PATTERNS)
+
+    async def _send_with_retry(
+        self,
+        chat_id: str,
+        content: str,
+        reply_to: Optional[str] = None,
+        metadata: Any = None,
+        max_retries: int = 2,
+        base_delay: float = 2.0,
+    ) -> "SendResult":
+        """
+        Send a message with automatic retry for transient network errors.
+
+        On permanent failures (e.g. formatting / permission errors) falls back
+        to a plain-text version before giving up. If all attempts fail due to
+        network errors, sends the user a brief delivery-failure notice so they
+        know to retry rather than waiting indefinitely.
+        """
+
+        result = await self.send(
+            chat_id=chat_id,
+            content=content,
+            reply_to=reply_to,
+            metadata=metadata,
+        )
+
+        if result.success:
+            return result
+
+        error_str = result.error or ""
+        is_network = result.retryable or self._is_retryable_error(error_str)
+
+        if is_network:
+            # Retry with exponential backoff for transient errors
+            for attempt in range(1, max_retries + 1):
+                delay = base_delay * (2 ** (attempt - 1)) + random.uniform(0, 1)
+                logger.warning(
+                    "[%s] Send failed (attempt %d/%d, retrying in %.1fs): %s",
+                    self.name, attempt, max_retries, delay, error_str,
+                )
+                await asyncio.sleep(delay)
+                result = await self.send(
+                    chat_id=chat_id,
+                    content=content,
+                    reply_to=reply_to,
+                    metadata=metadata,
+                )
+                if result.success:
+                    logger.info("[%s] Send succeeded on retry %d", self.name, attempt)
+                    return result
+                error_str = result.error or ""
+                if not (result.retryable or self._is_retryable_error(error_str)):
+                    break  # error switched to non-transient — fall through to plain-text fallback
+            else:
+                # All retries exhausted (loop completed without break) — notify user
+                logger.error("[%s] Failed to deliver response after %d retries: %s", self.name, max_retries, error_str)
+                notice = (
+                    "\u26a0\ufe0f Message delivery failed after multiple attempts. "
+                    "Please try again \u2014 your request was processed but the response could not be sent."
+                )
+                try:
+                    await self.send(chat_id=chat_id, content=notice, reply_to=reply_to, metadata=metadata)
+                except Exception as notify_err:
+                    logger.debug("[%s] Could not send delivery-failure notice: %s", self.name, notify_err)
+                return result
+
+        # Non-network / post-retry formatting failure: try plain text as fallback
+        logger.warning("[%s] Send failed: %s — trying plain-text fallback", self.name, error_str)
+        fallback_result = await self.send(
+            chat_id=chat_id,
+            content=f"(Response formatting failed, plain text:)\n\n{content[:3500]}",
+            reply_to=reply_to,
+            metadata=metadata,
+        )
+        if not fallback_result.success:
+            logger.error("[%s] Fallback send also failed: %s", self.name, fallback_result.error)
+        return fallback_result
+
    async def handle_message(self, event: MessageEvent) -> None:
        """
        Process an incoming message.
@@ -982,26 +1132,13 @@ class BasePlatformAdapter(ABC):
                # Send the text portion
                if text_content:
                    logger.info("[%s] Sending response (%d chars) to %s", self.name, len(text_content), event.source.chat_id)
-                    result = await self.send(
+                    result = await self._send_with_retry(
                        chat_id=event.source.chat_id,
                        content=text_content,
                        reply_to=event.message_id,
                        metadata=_thread_metadata,
                    )

-                    # Log send failures (don't raise - user already saw tool progress)
-                    if not result.success:
-                        print(f"[{self.name}] Failed to send response: {result.error}")
-                        # Try sending without markdown as fallback
-                        fallback_result = await self.send(
-                            chat_id=event.source.chat_id,
-                            content=f"(Response formatting failed, plain text:)\n\n{text_content[:3500]}",
-                            reply_to=event.message_id,
-                            metadata=_thread_metadata,
-                        )
-                        if not fallback_result.success:
-                            print(f"[{self.name}] Fallback send also failed: {fallback_result.error}")
-
                # Human-like pacing delay between text and media
                human_delay = self._get_human_delay()

@@ -550,6 +550,22 @@ class DiscordAdapter(BasePlatformAdapter):
                            return
                    # "all" falls through to handle_message
                
+                # If the message @mentions other users but NOT the bot, the
+                # sender is talking to someone else — stay silent.  Only
+                # applies in server channels; in DMs the user is always
+                # talking to the bot (mentions are just references).
+                # Controlled by DISCORD_IGNORE_NO_MENTION (default: true).
+                _ignore_no_mention = os.getenv(
+                    "DISCORD_IGNORE_NO_MENTION", "true"
+                ).lower() in ("true", "1", "yes")
+                if _ignore_no_mention and message.mentions and not isinstance(message.channel, discord.DMChannel):
+                    _bot_mentioned = (
+                        self._client.user is not None
+                        and self._client.user in message.mentions
+                    )
+                    if not _bot_mentioned:
+                        return  # Talking to someone else, don't interrupt
+
                await self._handle_message(message)

            @self._client.event
@@ -2096,6 +2112,11 @@ class DiscordAdapter(BasePlatformAdapter):
        if pending_text_injection:
            event_text = f"{pending_text_injection}\n\n{event_text}" if event_text else pending_text_injection

+        # Defense-in-depth: prevent empty user messages from entering session
+        # (can happen when user sends @mention-only with no other text)
+        if not event_text or not event_text.strip():
+            event_text = "(The user sent a message with no text content)"
+
        event = MessageEvent(
            text=event_text,
            message_type=msg_type,
@@ -43,6 +43,20 @@ from gateway.platforms.base import (
 from gateway.config import Platform, PlatformConfig

 logger = logging.getLogger(__name__)
+# Automated sender patterns — emails from these are silently ignored
+_NOREPLY_PATTERNS = (
+    "noreply", "no-reply", "no_reply", "donotreply", "do-not-reply",
+    "mailer-daemon", "postmaster", "bounce", "notifications@",
+    "automated@", "auto-confirm", "auto-reply", "automailer",
+)
+
+# RFC headers that indicate bulk/automated mail
+_AUTOMATED_HEADERS = {
+    "Auto-Submitted": lambda v: v.lower() != "no",
+    "Precedence": lambda v: v.lower() in ("bulk", "list", "junk"),
+    "X-Auto-Response-Suppress": lambda v: bool(v),
+    "List-Unsubscribe": lambda v: bool(v),
+}

 # Gmail-safe max length per email body
 MAX_MESSAGE_LENGTH = 50_000
@@ -50,7 +64,17 @@ MAX_MESSAGE_LENGTH = 50_000
 # Supported image extensions for inline detection
 _IMAGE_EXTS = {".jpg", ".jpeg", ".png", ".gif", ".webp"}

-
+def _is_automated_sender(address: str, headers: dict) -> bool:
+    """Return True if this email is from an automated/noreply source."""
+    addr = address.lower()
+    if any(pattern in addr for pattern in _NOREPLY_PATTERNS):
+        return True
+    for header, check in _AUTOMATED_HEADERS.items():
+        value = headers.get(header, "")
+        if value and check(value):
+            return True
+    return False
+    
 def check_email_requirements() -> bool:
    """Check if email platform dependencies are available."""
    addr = os.getenv("EMAIL_ADDRESS")
@@ -213,6 +237,7 @@ class EmailAdapter(BasePlatformAdapter):

        # Track message IDs we've already processed to avoid duplicates
        self._seen_uids: set = set()
+        self._seen_uids_max: int = 2000   # cap to prevent unbounded memory growth
        self._poll_task: Optional[asyncio.Task] = None

        # Map chat_id (sender email) -> last subject + message-id for threading
@@ -220,6 +245,26 @@ class EmailAdapter(BasePlatformAdapter):

        logger.info("[Email] Adapter initialized for %s", self._address)

+    def _trim_seen_uids(self) -> None:
+        """Keep only the most recent UIDs to prevent unbounded memory growth.
+
+        IMAP UIDs are monotonically increasing integers. When the set grows
+        beyond the cap, we keep only the highest half — old UIDs are safe to
+        drop because new messages always have higher UIDs and IMAP's UNSEEN
+        flag prevents re-delivery regardless.
+        """
+        if len(self._seen_uids) <= self._seen_uids_max:
+            return
+        try:
+            # UIDs are bytes like b'1234' — sort numerically and keep top half
+            sorted_uids = sorted(self._seen_uids, key=lambda u: int(u))
+            keep = self._seen_uids_max // 2
+            self._seen_uids = set(sorted_uids[-keep:])
+            logger.debug("[Email] Trimmed seen UIDs to %d entries", len(self._seen_uids))
+        except (ValueError, TypeError):
+            # Fallback: just clear old entries if sort fails
+            self._seen_uids = set(list(self._seen_uids)[-self._seen_uids_max // 2:])
+
    async def connect(self) -> bool:
        """Connect to the IMAP server and start polling for new messages."""
        try:
@@ -232,6 +277,8 @@ class EmailAdapter(BasePlatformAdapter):
            if status == "OK" and data and data[0]:
                for uid in data[0].split():
                    self._seen_uids.add(uid)
+            # Keep only the most recent UIDs to prevent unbounded growth
+            self._trim_seen_uids()
            imap.logout()
            logger.info("[Email] IMAP connection test passed. %d existing messages skipped.", len(self._seen_uids))
        except Exception as e:
@@ -302,6 +349,9 @@ class EmailAdapter(BasePlatformAdapter):
                if uid in self._seen_uids:
                    continue
                self._seen_uids.add(uid)
+                # Trim periodically to prevent unbounded memory growth
+                if len(self._seen_uids) > self._seen_uids_max:
+                    self._trim_seen_uids()

                status, msg_data = imap.uid("fetch", uid, "(RFC822)")
                if status != "OK":
@@ -320,6 +370,11 @@ class EmailAdapter(BasePlatformAdapter):
                subject = _decode_header_value(msg.get("Subject", "(no subject)"))
                message_id = msg.get("Message-ID", "")
                in_reply_to = msg.get("In-Reply-To", "")
+                # Skip automated/noreply senders before any processing
+                msg_headers = dict(msg.items())
+                if _is_automated_sender(sender_addr, msg_headers):
+                    logger.debug("[Email] Skipping automated sender: %s", sender_addr)
+                    continue
                body = _extract_text_body(msg)
                attachments = _extract_attachments(msg, skip_attachments=self._skip_attachments)

@@ -348,6 +403,11 @@ class EmailAdapter(BasePlatformAdapter):
        if sender_addr == self._address.lower():
            return

+        # Never reply to automated senders
+        if _is_automated_sender(sender_addr, {}):
+            logger.debug("[Email] Dropping automated sender at dispatch: %s", sender_addr)
+            return
+
        subject = msg_data["subject"]
        body = msg_data["body"].strip()
        attachments = msg_data["attachments"]
@@ -40,7 +40,9 @@ logger = logging.getLogger(__name__)
 MAX_MESSAGE_LENGTH = 4000

 # Store directory for E2EE keys and sync state.
-_STORE_DIR = Path.home() / ".hermes" / "matrix" / "store"
+# Uses get_hermes_home() so each profile gets its own Matrix store.
+from hermes_constants import get_hermes_dir as _get_hermes_dir
+_STORE_DIR = _get_hermes_dir("platforms/matrix/store", "matrix/store")

 # Grace period: ignore messages older than this many seconds before startup.
 _STARTUP_GRACE_SECONDS = 5
@@ -161,22 +163,49 @@ class MatrixAdapter(BasePlatformAdapter):
        # Authenticate.
        if self._access_token:
            client.access_token = self._access_token
-            # Resolve user_id if not set.
-            if not self._user_id:
-                resp = await client.whoami()
-                if isinstance(resp, nio.WhoamiResponse):
-                    self._user_id = resp.user_id
-                    client.user_id = resp.user_id
-                    logger.info("Matrix: authenticated as %s", self._user_id)
-                else:
-                    logger.error(
-                        "Matrix: whoami failed — check MATRIX_ACCESS_TOKEN and MATRIX_HOMESERVER"
+
+            # With access-token auth, always resolve whoami so we validate the
+            # token and learn the device_id. The device_id matters for E2EE:
+            # without it, matrix-nio can send plain messages but may fail to
+            # decrypt inbound encrypted events or encrypt outbound room sends.
+            resp = await client.whoami()
+            if isinstance(resp, nio.WhoamiResponse):
+                resolved_user_id = getattr(resp, "user_id", "") or self._user_id
+                resolved_device_id = getattr(resp, "device_id", "")
+                if resolved_user_id:
+                    self._user_id = resolved_user_id
+
+                # restore_login() is the matrix-nio path that binds the access
+                # token to a specific device and loads the crypto store.
+                if resolved_device_id and hasattr(client, "restore_login"):
+                    client.restore_login(
+                        self._user_id or resolved_user_id,
+                        resolved_device_id,
+                        self._access_token,
                    )
-                    await client.close()
-                    return False
+                else:
+                    if self._user_id:
+                        client.user_id = self._user_id
+                    if resolved_device_id:
+                        client.device_id = resolved_device_id
+                    client.access_token = self._access_token
+                    if self._encryption:
+                        logger.warning(
+                            "Matrix: access-token login did not restore E2EE state; "
+                            "encrypted rooms may fail until a device_id is available"
+                        )
+
+                logger.info(
+                    "Matrix: using access token for %s%s",
+                    self._user_id or "(unknown user)",
+                    f" (device {resolved_device_id})" if resolved_device_id else "",
+                )
            else:
-                client.user_id = self._user_id
-                logger.info("Matrix: using access token for %s", self._user_id)
+                logger.error(
+                    "Matrix: whoami failed — check MATRIX_ACCESS_TOKEN and MATRIX_HOMESERVER"
+                )
+                await client.close()
+                return False
        elif self._password and self._user_id:
            resp = await client.login(
                self._password,
@@ -194,13 +223,18 @@ class MatrixAdapter(BasePlatformAdapter):
            return False

        # If E2EE is enabled, load the crypto store.
-        if self._encryption and hasattr(client, "olm"):
+        if self._encryption and getattr(client, "olm", None):
            try:
                if client.should_upload_keys:
                    await client.keys_upload()
                logger.info("Matrix: E2EE crypto initialized")
            except Exception as exc:
                logger.warning("Matrix: crypto init issue: %s", exc)
+        elif self._encryption:
+            logger.warning(
+                "Matrix: E2EE requested but crypto store is not loaded; "
+                "encrypted rooms may fail"
+            )

        # Register event callbacks.
        client.add_event_callback(self._on_room_message, nio.RoomMessageText)
@@ -230,6 +264,7 @@ class MatrixAdapter(BasePlatformAdapter):
            )
            # Build DM room cache from m.direct account data.
            await self._refresh_dm_cache()
+            await self._run_e2ee_maintenance()
        else:
            logger.warning("Matrix: initial sync returned %s", type(resp).__name__)

@@ -301,13 +336,48 @@ class MatrixAdapter(BasePlatformAdapter):
                    relates_to["m.in_reply_to"] = {"event_id": reply_to}
                msg_content["m.relates_to"] = relates_to

-            resp = await self._client.room_send(
-                chat_id,
-                "m.room.message",
-                msg_content,
-            )
+            async def _room_send_once(*, ignore_unverified_devices: bool = False):
+                return await asyncio.wait_for(
+                    self._client.room_send(
+                        chat_id,
+                        "m.room.message",
+                        msg_content,
+                        ignore_unverified_devices=ignore_unverified_devices,
+                    ),
+                    timeout=45,
+                )
+
+            try:
+                resp = await _room_send_once(ignore_unverified_devices=False)
+            except Exception as exc:
+                retryable = isinstance(exc, asyncio.TimeoutError)
+                olm_unverified = getattr(nio, "OlmUnverifiedDeviceError", None)
+                send_retry = getattr(nio, "SendRetryError", None)
+                if isinstance(olm_unverified, type) and isinstance(exc, olm_unverified):
+                    retryable = True
+                if isinstance(send_retry, type) and isinstance(exc, send_retry):
+                    retryable = True
+
+                if not retryable:
+                    logger.error("Matrix: failed to send to %s: %s", chat_id, exc)
+                    return SendResult(success=False, error=str(exc))
+
+                logger.warning(
+                    "Matrix: initial encrypted send to %s failed (%s); "
+                    "retrying after E2EE maintenance with ignored unverified devices",
+                    chat_id,
+                    exc,
+                )
+                await self._run_e2ee_maintenance()
+                try:
+                    resp = await _room_send_once(ignore_unverified_devices=True)
+                except Exception as retry_exc:
+                    logger.error("Matrix: failed to send to %s after retry: %s", chat_id, retry_exc)
+                    return SendResult(success=False, error=str(retry_exc))
+
            if isinstance(resp, nio.RoomSendResponse):
                last_event_id = resp.event_id
+                logger.info("Matrix: sent event %s to %s", last_event_id, chat_id)
            else:
                err = getattr(resp, "message", str(resp))
                logger.error("Matrix: failed to send to %s: %s", chat_id, err)
@@ -551,9 +621,23 @@ class MatrixAdapter(BasePlatformAdapter):

    async def _sync_loop(self) -> None:
        """Continuously sync with the homeserver."""
+        import nio
+
        while not self._closing:
            try:
-                await self._client.sync(timeout=30000)
+                resp = await self._client.sync(timeout=30000)
+                if isinstance(resp, nio.SyncError):
+                    if self._closing:
+                        return
+                    logger.warning(
+                        "Matrix: sync returned %s: %s — retrying in 5s",
+                        type(resp).__name__,
+                        getattr(resp, "message", resp),
+                    )
+                    await asyncio.sleep(5)
+                    continue
+
+                await self._run_e2ee_maintenance()
            except asyncio.CancelledError:
                return
            except Exception as exc:
@@ -562,6 +646,38 @@ class MatrixAdapter(BasePlatformAdapter):
                logger.warning("Matrix: sync error: %s — retrying in 5s", exc)
                await asyncio.sleep(5)

+    async def _run_e2ee_maintenance(self) -> None:
+        """Run matrix-nio E2EE housekeeping between syncs.
+
+        Hermes uses a custom sync loop instead of matrix-nio's sync_forever(),
+        so we need to explicitly drive the key management work that sync_forever()
+        normally handles for encrypted rooms.
+        """
+        client = self._client
+        if not client or not self._encryption or not getattr(client, "olm", None):
+            return
+
+        tasks = [asyncio.create_task(client.send_to_device_messages())]
+
+        if client.should_upload_keys:
+            tasks.append(asyncio.create_task(client.keys_upload()))
+
+        if client.should_query_keys:
+            tasks.append(asyncio.create_task(client.keys_query()))
+
+        if client.should_claim_keys:
+            users = client.get_users_for_key_claiming()
+            if users:
+                tasks.append(asyncio.create_task(client.keys_claim(users)))
+
+        for task in asyncio.as_completed(tasks):
+            try:
+                await task
+            except asyncio.CancelledError:
+                raise
+            except Exception as exc:
+                logger.warning("Matrix: E2EE maintenance task failed: %s", exc)
+
    # ------------------------------------------------------------------
    # Event callbacks
    # ------------------------------------------------------------------
@@ -407,18 +407,38 @@ class MattermostAdapter(BasePlatformAdapter):
        kind: str = "file",
    ) -> SendResult:
        """Download a URL and upload it as a file attachment."""
+        import asyncio
        import aiohttp
-        try:
-            async with self._session.get(url, timeout=aiohttp.ClientTimeout(total=30)) as resp:
-                if resp.status >= 400:
-                    # Fall back to sending the URL as text.
-                    return await self.send(chat_id, f"{caption or ''}\n{url}".strip(), reply_to)
-                file_data = await resp.read()
-                ct = resp.content_type or "application/octet-stream"
-                # Derive filename from URL.
-                fname = url.rsplit("/", 1)[-1].split("?")[0] or f"{kind}.png"
-        except Exception as exc:
-            logger.warning("Mattermost: failed to download %s: %s", url, exc)
+
+        last_exc = None
+        file_data = None
+        ct = "application/octet-stream"
+        fname = url.rsplit("/", 1)[-1].split("?")[0] or f"{kind}.png"
+
+        for attempt in range(3):
+            try:
+                async with self._session.get(url, timeout=aiohttp.ClientTimeout(total=30)) as resp:
+                    if resp.status >= 500 or resp.status == 429:
+                        if attempt < 2:
+                            logger.debug("Mattermost download retry %d/2 for %s (status %d)",
+                                         attempt + 1, url[:80], resp.status)
+                            await asyncio.sleep(1.5 * (attempt + 1))
+                            continue
+                    if resp.status >= 400:
+                        return await self.send(chat_id, f"{caption or ''}\n{url}".strip(), reply_to)
+                    file_data = await resp.read()
+                    ct = resp.content_type or "application/octet-stream"
+                    break
+            except (aiohttp.ClientError, asyncio.TimeoutError) as exc:
+                last_exc = exc
+                if attempt < 2:
+                    await asyncio.sleep(1.5 * (attempt + 1))
+                    continue
+                logger.warning("Mattermost: failed to download %s after %d attempts: %s", url, attempt + 1, exc)
+                return await self.send(chat_id, f"{caption or ''}\n{url}".strip(), reply_to)
+
+        if file_data is None:
+            logger.warning("Mattermost: download returned no data for %s", url)
            return await self.send(chat_id, f"{caption or ''}\n{url}".strip(), reply_to)

        file_id = await self._upload_file(chat_id, file_data, fname, ct)
@@ -583,9 +603,19 @@ class MattermostAdapter(BasePlatformAdapter):
        # For DMs, user_id is sufficient.  For channels, check for @mention.
        message_text = post.get("message", "")

-        # Mention-only mode: skip channel messages that don't @mention the bot.
-        # DMs (type "D") are always processed.
+        # Mention-gating for non-DM channels.
+        # Config (env vars):
+        #   MATTERMOST_REQUIRE_MENTION: Require @mention in channels (default: true)
+        #   MATTERMOST_FREE_RESPONSE_CHANNELS: Channel IDs where bot responds without mention
        if channel_type_raw != "D":
+            require_mention = os.getenv(
+                "MATTERMOST_REQUIRE_MENTION", "true"
+            ).lower() not in ("false", "0", "no")
+
+            free_channels_raw = os.getenv("MATTERMOST_FREE_RESPONSE_CHANNELS", "")
+            free_channels = {ch.strip() for ch in free_channels_raw.split(",") if ch.strip()}
+            is_free_channel = channel_id in free_channels
+
            mention_patterns = [
                f"@{self._bot_username}",
                f"@{self._bot_user_id}",
@@ -594,13 +624,21 @@ class MattermostAdapter(BasePlatformAdapter):
                pattern.lower() in message_text.lower()
                for pattern in mention_patterns
            )
-            if not has_mention:
+
+            if require_mention and not is_free_channel and not has_mention:
                logger.debug(
                    "Mattermost: skipping non-DM message without @mention (channel=%s)",
                    channel_id,
                )
                return

+            # Strip @mention from the message text so the agent sees clean input.
+            if has_mention:
+                for pattern in mention_patterns:
+                    message_text = re.sub(
+                        re.escape(pattern), "", message_text, flags=re.IGNORECASE
+                    ).strip()
+
        # Resolve sender info.
        sender_id = post.get("user_id", "")
        sender_name = data.get("sender_name", "").lstrip("@") or sender_id
@@ -279,6 +279,12 @@ class SignalAdapter(BasePlatformAdapter):
                            line = line.strip()
                            if not line:
                                continue
+                            # SSE keepalive comments (":") prove the connection
+                            # is alive — update activity so the health monitor
+                            # doesn't report false idle warnings.
+                            if line.startswith(":"):
+                                self._last_sse_activity = time.time()
+                                continue
                            # Parse SSE data lines
                            if line.startswith("data:"):
                                data_str = line[5:].strip()
@@ -819,33 +819,65 @@ class SlackAdapter(BasePlatformAdapter):
        await self.handle_message(event)

    async def _download_slack_file(self, url: str, ext: str, audio: bool = False) -> str:
-        """Download a Slack file using the bot token for auth."""
+        """Download a Slack file using the bot token for auth, with retry."""
+        import asyncio
        import httpx

        bot_token = self.config.token
-        async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
-            response = await client.get(
-                url,
-                headers={"Authorization": f"Bearer {bot_token}"},
-            )
-            response.raise_for_status()
+        last_exc = None

-        if audio:
-            from gateway.platforms.base import cache_audio_from_bytes
-            return cache_audio_from_bytes(response.content, ext)
-        else:
-            from gateway.platforms.base import cache_image_from_bytes
-            return cache_image_from_bytes(response.content, ext)
+        async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
+            for attempt in range(3):
+                try:
+                    response = await client.get(
+                        url,
+                        headers={"Authorization": f"Bearer {bot_token}"},
+                    )
+                    response.raise_for_status()
+
+                    if audio:
+                        from gateway.platforms.base import cache_audio_from_bytes
+                        return cache_audio_from_bytes(response.content, ext)
+                    else:
+                        from gateway.platforms.base import cache_image_from_bytes
+                        return cache_image_from_bytes(response.content, ext)
+                except (httpx.TimeoutException, httpx.HTTPStatusError) as exc:
+                    last_exc = exc
+                    if isinstance(exc, httpx.HTTPStatusError) and exc.response.status_code < 429:
+                        raise
+                    if attempt < 2:
+                        logger.debug("Slack file download retry %d/2 for %s: %s",
+                                     attempt + 1, url[:80], exc)
+                        await asyncio.sleep(1.5 * (attempt + 1))
+                        continue
+                    raise
+        raise last_exc

    async def _download_slack_file_bytes(self, url: str) -> bytes:
-        """Download a Slack file and return raw bytes."""
+        """Download a Slack file and return raw bytes, with retry."""
+        import asyncio
        import httpx

        bot_token = self.config.token
+        last_exc = None
+
        async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
-            response = await client.get(
-                url,
-                headers={"Authorization": f"Bearer {bot_token}"},
-            )
-            response.raise_for_status()
-        return response.content
+            for attempt in range(3):
+                try:
+                    response = await client.get(
+                        url,
+                        headers={"Authorization": f"Bearer {bot_token}"},
+                    )
+                    response.raise_for_status()
+                    return response.content
+                except (httpx.TimeoutException, httpx.HTTPStatusError) as exc:
+                    last_exc = exc
+                    if isinstance(exc, httpx.HTTPStatusError) and exc.response.status_code < 429:
+                        raise
+                    if attempt < 2:
+                        logger.debug("Slack file download retry %d/2 for %s: %s",
+                                     attempt + 1, url[:80], exc)
+                        await asyncio.sleep(1.5 * (attempt + 1))
+                        continue
+                    raise
+        raise last_exc
@@ -11,7 +11,7 @@ import asyncio
 import logging
 import os
 import re
-from typing import Dict, Optional, Any
+from typing import Dict, List, Optional, Any

 logger = logging.getLogger(__name__)

@@ -25,6 +25,7 @@ try:
        filters,
    )
    from telegram.constants import ParseMode, ChatType
+    from telegram.request import HTTPXRequest
    TELEGRAM_AVAILABLE = True
 except ImportError:
    TELEGRAM_AVAILABLE = False
@@ -34,6 +35,7 @@ except ImportError:
    Application = Any
    CommandHandler = Any
    TelegramMessageHandler = Any
+    HTTPXRequest = Any
    filters = None
    ParseMode = None
    ChatType = None
@@ -59,6 +61,11 @@ from gateway.platforms.base import (
    cache_document_from_bytes,
    SUPPORTED_DOCUMENT_TYPES,
 )
+from gateway.platforms.telegram_network import (
+    TelegramFallbackTransport,
+    discover_fallback_ips,
+    parse_fallback_ip_env,
+)


 def check_telegram_requirements() -> bool:
@@ -138,6 +145,13 @@ class TelegramAdapter(BasePlatformAdapter):
        # DM Topics config from extra.dm_topics
        self._dm_topics_config: List[Dict[str, Any]] = self.config.extra.get("dm_topics", [])

+    def _fallback_ips(self) -> list[str]:
+        """Return validated fallback IPs from config (populated by _apply_env_overrides)."""
+        configured = self.config.extra.get("fallback_ips", []) if getattr(self.config, "extra", None) else []
+        if isinstance(configured, str):
+            configured = configured.split(",")
+        return parse_fallback_ip_env(",".join(str(v) for v in configured) if configured else None)
+
    @staticmethod
    def _looks_like_polling_conflict(error: Exception) -> bool:
        text = str(error).lower()
@@ -331,7 +345,8 @@ class TelegramAdapter(BasePlatformAdapter):
    def _persist_dm_topic_thread_id(self, chat_id: int, topic_name: str, thread_id: int) -> None:
        """Save a newly created thread_id back into config.yaml so it persists across restarts."""
        try:
-            config_path = _Path.home() / ".hermes" / "config.yaml"
+            from hermes_constants import get_hermes_home
+            config_path = get_hermes_home() / "config.yaml"
            if not config_path.exists():
                logger.warning("[%s] Config file not found at %s, cannot persist thread_id", self.name, config_path)
                return
@@ -474,7 +489,26 @@ class TelegramAdapter(BasePlatformAdapter):
                return False

            # Build the application
-            self._app = Application.builder().token(self.config.token).build()
+            builder = Application.builder().token(self.config.token)
+            fallback_ips = self._fallback_ips()
+            if not fallback_ips:
+                fallback_ips = await discover_fallback_ips()
+                logger.info(
+                    "[%s] Auto-discovered Telegram fallback IPs: %s",
+                    self.name,
+                    ", ".join(fallback_ips),
+                )
+            if fallback_ips:
+                logger.warning(
+                    "[%s] Telegram fallback IPs active: %s",
+                    self.name,
+                    ", ".join(fallback_ips),
+                )
+                transport = TelegramFallbackTransport(fallback_ips)
+                request = HTTPXRequest(httpx_kwargs={"transport": transport})
+                get_updates_request = HTTPXRequest(httpx_kwargs={"transport": transport})
+                builder = builder.request(request).get_updates_request(get_updates_request)
+            self._app = builder.build()
            self._bot = self._app.bot
            
            # Register handlers
@@ -674,9 +708,15 @@ class TelegramAdapter(BasePlatformAdapter):
            except ImportError:
                _NetErr = OSError  # type: ignore[misc,assignment]

+            try:
+                from telegram.error import BadRequest as _BadReq
+            except ImportError:
+                _BadReq = None  # type: ignore[assignment,misc]
+
            for i, chunk in enumerate(chunks):
                should_thread = self._should_thread_reply(reply_to, i)
                reply_to_id = int(reply_to) if should_thread else None
+                effective_thread_id = int(thread_id) if thread_id else None

                msg = None
                for _send_attempt in range(3):
@@ -688,7 +728,7 @@ class TelegramAdapter(BasePlatformAdapter):
                                text=chunk,
                                parse_mode=ParseMode.MARKDOWN_V2,
                                reply_to_message_id=reply_to_id,
-                                message_thread_id=int(thread_id) if thread_id else None,
+                                message_thread_id=effective_thread_id,
                            )
                        except Exception as md_error:
                            # Markdown parsing failed, try plain text
@@ -700,12 +740,30 @@ class TelegramAdapter(BasePlatformAdapter):
                                    text=plain_chunk,
                                    parse_mode=None,
                                    reply_to_message_id=reply_to_id,
-                                    message_thread_id=int(thread_id) if thread_id else None,
+                                    message_thread_id=effective_thread_id,
                                )
                            else:
                                raise
                        break  # success
                    except _NetErr as send_err:
+                        # BadRequest is a subclass of NetworkError in
+                        # python-telegram-bot but represents permanent errors
+                        # (not transient network issues). Detect and handle
+                        # specific cases instead of blindly retrying.
+                        if _BadReq and isinstance(send_err, _BadReq):
+                            err_lower = str(send_err).lower()
+                            if "thread not found" in err_lower and effective_thread_id is not None:
+                                # Thread doesn't exist — retry without
+                                # message_thread_id so the message still
+                                # reaches the chat.
+                                logger.warning(
+                                    "[%s] Thread %s not found, retrying without message_thread_id",
+                                    self.name, effective_thread_id,
+                                )
+                                effective_thread_id = None
+                                continue
+                            # Other BadRequest errors are permanent — don't retry
+                            raise
                        if _send_attempt < 2:
                            wait = 2 ** _send_attempt
                            logger.warning("[%s] Network error on send (attempt %d/3), retrying in %ds: %s",
@@ -1700,7 +1758,8 @@ class TelegramAdapter(BasePlatformAdapter):
        recognized without a gateway restart.
        """
        try:
-            config_path = _Path.home() / ".hermes" / "config.yaml"
+            from hermes_constants import get_hermes_home
+            config_path = get_hermes_home() / "config.yaml"
            if not config_path.exists():
                return

@@ -0,0 +1,245 @@
+"""Telegram-specific network helpers.
+
+Provides a hostname-preserving fallback transport for networks where
+api.telegram.org resolves to an endpoint that is unreachable from the current
+host. The transport keeps the logical request host and TLS SNI as
+api.telegram.org while retrying the TCP connection against one or more fallback
+IPv4 addresses.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import ipaddress
+import logging
+import os
+import socket
+from typing import Iterable, Optional
+
+import httpx
+
+logger = logging.getLogger(__name__)
+
+_TELEGRAM_API_HOST = "api.telegram.org"
+
+# DNS-over-HTTPS providers used to discover Telegram API IPs that may differ
+# from the (potentially unreachable) IP returned by the local system resolver.
+_DOH_TIMEOUT = 4.0  # seconds — bounded so connect() isn't noticeably delayed
+
+_DOH_PROVIDERS: list[dict] = [
+    {
+        "url": "https://dns.google/resolve",
+        "params": {"name": _TELEGRAM_API_HOST, "type": "A"},
+        "headers": {},
+    },
+    {
+        "url": "https://cloudflare-dns.com/dns-query",
+        "params": {"name": _TELEGRAM_API_HOST, "type": "A"},
+        "headers": {"Accept": "application/dns-json"},
+    },
+]
+
+# Last-resort IPs when DoH is also blocked.  These are stable Telegram Bot API
+# endpoints in the 149.154.160.0/20 block (same seed used by OpenClaw).
+_SEED_FALLBACK_IPS: list[str] = ["149.154.167.220"]
+
+
+def _resolve_proxy_url() -> str | None:
+    for key in ("HTTPS_PROXY", "HTTP_PROXY", "ALL_PROXY", "https_proxy", "http_proxy", "all_proxy"):
+        value = (os.environ.get(key) or "").strip()
+        if value:
+            return value
+    return None
+
+
+class TelegramFallbackTransport(httpx.AsyncBaseTransport):
+    """Retry Telegram Bot API requests via fallback IPs while preserving TLS/SNI.
+
+    Requests continue to target https://api.telegram.org/... logically, but on
+    connect failures the underlying TCP connection is retried against a known
+    reachable IP. This is effectively the programmatic equivalent of
+    ``curl --resolve api.telegram.org:443:<ip>``.
+    """
+
+    def __init__(self, fallback_ips: Iterable[str], **transport_kwargs):
+        self._fallback_ips = [ip for ip in dict.fromkeys(_normalize_fallback_ips(fallback_ips))]
+        proxy_url = _resolve_proxy_url()
+        if proxy_url and "proxy" not in transport_kwargs:
+            transport_kwargs["proxy"] = proxy_url
+        self._primary = httpx.AsyncHTTPTransport(**transport_kwargs)
+        self._fallbacks = {
+            ip: httpx.AsyncHTTPTransport(**transport_kwargs) for ip in self._fallback_ips
+        }
+        self._sticky_ip: Optional[str] = None
+        self._sticky_lock = asyncio.Lock()
+
+    async def handle_async_request(self, request: httpx.Request) -> httpx.Response:
+        if request.url.host != _TELEGRAM_API_HOST or not self._fallback_ips:
+            return await self._primary.handle_async_request(request)
+
+        sticky_ip = self._sticky_ip
+        attempt_order: list[Optional[str]] = [sticky_ip] if sticky_ip else [None]
+        for ip in self._fallback_ips:
+            if ip != sticky_ip:
+                attempt_order.append(ip)
+
+        last_error: Exception | None = None
+        for ip in attempt_order:
+            candidate = request if ip is None else _rewrite_request_for_ip(request, ip)
+            transport = self._primary if ip is None else self._fallbacks[ip]
+            try:
+                response = await transport.handle_async_request(candidate)
+                if ip is not None and self._sticky_ip != ip:
+                    async with self._sticky_lock:
+                        if self._sticky_ip != ip:
+                            self._sticky_ip = ip
+                            logger.warning(
+                                "[Telegram] Primary api.telegram.org path unreachable; using sticky fallback IP %s",
+                                ip,
+                            )
+                return response
+            except Exception as exc:
+                last_error = exc
+                if not _is_retryable_connect_error(exc):
+                    raise
+                if ip is None:
+                    logger.warning(
+                        "[Telegram] Primary api.telegram.org connection failed (%s); trying fallback IPs %s",
+                        exc,
+                        ", ".join(self._fallback_ips),
+                    )
+                    continue
+                logger.warning("[Telegram] Fallback IP %s failed: %s", ip, exc)
+                continue
+
+        assert last_error is not None
+        raise last_error
+
+    async def aclose(self) -> None:
+        await self._primary.aclose()
+        for transport in self._fallbacks.values():
+            await transport.aclose()
+
+
+def _normalize_fallback_ips(values: Iterable[str]) -> list[str]:
+    normalized: list[str] = []
+    for value in values:
+        raw = str(value).strip()
+        if not raw:
+            continue
+        try:
+            addr = ipaddress.ip_address(raw)
+        except ValueError:
+            logger.warning("Ignoring invalid Telegram fallback IP: %r", raw)
+            continue
+        if addr.version != 4:
+            logger.warning("Ignoring non-IPv4 Telegram fallback IP: %s", raw)
+            continue
+        normalized.append(str(addr))
+    return normalized
+
+
+def parse_fallback_ip_env(value: str | None) -> list[str]:
+    if not value:
+        return []
+    parts = [part.strip() for part in value.split(",")]
+    return _normalize_fallback_ips(parts)
+
+
+def _resolve_system_dns() -> set[str]:
+    """Return the IPv4 addresses that the OS resolver gives for api.telegram.org."""
+    try:
+        results = socket.getaddrinfo(_TELEGRAM_API_HOST, 443, socket.AF_INET)
+        return {addr[4][0] for addr in results}
+    except Exception:
+        return set()
+
+
+async def _query_doh_provider(
+    client: httpx.AsyncClient, provider: dict
+) -> list[str]:
+    """Query one DoH provider and return A-record IPs."""
+    try:
+        resp = await client.get(
+            provider["url"], params=provider["params"], headers=provider["headers"]
+        )
+        resp.raise_for_status()
+        data = resp.json()
+        ips: list[str] = []
+        for answer in data.get("Answer", []):
+            if answer.get("type") != 1:  # A record
+                continue
+            raw = answer.get("data", "").strip()
+            try:
+                ipaddress.ip_address(raw)
+                ips.append(raw)
+            except ValueError:
+                continue
+        return ips
+    except Exception as exc:
+        logger.debug("DoH query to %s failed: %s", provider["url"], exc)
+        return []
+
+
+async def discover_fallback_ips() -> list[str]:
+    """Auto-discover Telegram API IPs via DNS-over-HTTPS.
+
+    Resolves api.telegram.org through Google and Cloudflare DoH, collects all
+    unique IPs, and excludes the system-DNS-resolved IP (which is presumably
+    unreachable on this network).  Falls back to a hardcoded seed list when DoH
+    is also unavailable.
+    """
+    async with httpx.AsyncClient(timeout=httpx.Timeout(_DOH_TIMEOUT)) as client:
+        doh_tasks = [_query_doh_provider(client, p) for p in _DOH_PROVIDERS]
+        system_dns_task = asyncio.to_thread(_resolve_system_dns)
+        results = await asyncio.gather(system_dns_task, *doh_tasks, return_exceptions=True)
+
+    # results[0] = system DNS IPs (set), results[1:] = DoH IP lists
+    system_ips: set[str] = results[0] if isinstance(results[0], set) else set()
+
+    doh_ips: list[str] = []
+    for r in results[1:]:
+        if isinstance(r, list):
+            doh_ips.extend(r)
+
+    # Deduplicate preserving order, exclude system-DNS IPs
+    seen: set[str] = set()
+    candidates: list[str] = []
+    for ip in doh_ips:
+        if ip not in seen and ip not in system_ips:
+            seen.add(ip)
+            candidates.append(ip)
+
+    # Validate through existing normalization
+    validated = _normalize_fallback_ips(candidates)
+
+    if validated:
+        logger.debug("Discovered Telegram fallback IPs via DoH: %s", ", ".join(validated))
+        return validated
+
+    logger.info(
+        "DoH discovery yielded no new IPs (system DNS: %s); using seed fallback IPs %s",
+        ", ".join(system_ips) or "unknown",
+        ", ".join(_SEED_FALLBACK_IPS),
+    )
+    return list(_SEED_FALLBACK_IPS)
+
+
+def _rewrite_request_for_ip(request: httpx.Request, ip: str) -> httpx.Request:
+    original_host = request.url.host or _TELEGRAM_API_HOST
+    url = request.url.copy_with(host=ip)
+    headers = request.headers.copy()
+    headers["host"] = original_host
+    extensions = dict(request.extensions)
+    extensions["sni_hostname"] = original_host
+    return httpx.Request(
+        method=request.method,
+        url=url,
+        headers=headers,
+        stream=request.stream,
+        extensions=extensions,
+    )
+
+
+def _is_retryable_connect_error(exc: Exception) -> bool:
+    return isinstance(exc, (httpx.ConnectTimeout, httpx.ConnectError))
@@ -27,6 +27,7 @@ import hashlib
 import hmac
 import json
 import logging
+import os
 import re
 import subprocess
 import time
@@ -53,6 +54,7 @@ logger = logging.getLogger(__name__)
 DEFAULT_HOST = "0.0.0.0"
 DEFAULT_PORT = 8644
 _INSECURE_NO_AUTH = "INSECURE_NO_AUTH"
+_DYNAMIC_ROUTES_FILENAME = "webhook_subscriptions.json"


 def check_webhook_requirements() -> bool:
@@ -68,7 +70,10 @@ class WebhookAdapter(BasePlatformAdapter):
        self._host: str = config.extra.get("host", DEFAULT_HOST)
        self._port: int = int(config.extra.get("port", DEFAULT_PORT))
        self._global_secret: str = config.extra.get("secret", "")
-        self._routes: Dict[str, dict] = config.extra.get("routes", {})
+        self._static_routes: Dict[str, dict] = config.extra.get("routes", {})
+        self._dynamic_routes: Dict[str, dict] = {}
+        self._dynamic_routes_mtime: float = 0.0
+        self._routes: Dict[str, dict] = dict(self._static_routes)
        self._runner = None

        # Delivery info keyed by session chat_id — consumed by send()
@@ -96,6 +101,9 @@ class WebhookAdapter(BasePlatformAdapter):
    # ------------------------------------------------------------------

    async def connect(self) -> bool:
+        # Load agent-created subscriptions before validating
+        self._reload_dynamic_routes()
+
        # Validate routes at startup — secret is required per route
        for name, route in self._routes.items():
            secret = route.get("secret", self._global_secret)
@@ -182,8 +190,46 @@ class WebhookAdapter(BasePlatformAdapter):
        """GET /health — simple health check."""
        return web.json_response({"status": "ok", "platform": "webhook"})

+    def _reload_dynamic_routes(self) -> None:
+        """Reload agent-created subscriptions from disk if the file changed."""
+        from pathlib import Path as _Path
+        hermes_home = _Path(
+            os.getenv("HERMES_HOME", str(_Path.home() / ".hermes"))
+        ).expanduser()
+        subs_path = hermes_home / _DYNAMIC_ROUTES_FILENAME
+        if not subs_path.exists():
+            if self._dynamic_routes:
+                self._dynamic_routes = {}
+                self._routes = dict(self._static_routes)
+                logger.debug("[webhook] Dynamic subscriptions file removed, cleared dynamic routes")
+            return
+        try:
+            mtime = subs_path.stat().st_mtime
+            if mtime <= self._dynamic_routes_mtime:
+                return  # No change
+            data = json.loads(subs_path.read_text(encoding="utf-8"))
+            if not isinstance(data, dict):
+                return
+            # Merge: static routes take precedence over dynamic ones
+            self._dynamic_routes = {
+                k: v for k, v in data.items()
+                if k not in self._static_routes
+            }
+            self._routes = {**self._dynamic_routes, **self._static_routes}
+            self._dynamic_routes_mtime = mtime
+            logger.info(
+                "[webhook] Reloaded %d dynamic route(s): %s",
+                len(self._dynamic_routes),
+                ", ".join(self._dynamic_routes.keys()) or "(none)",
+            )
+        except Exception as e:
+            logger.warning("[webhook] Failed to reload dynamic routes: %s", e)
+
    async def _handle_webhook(self, request: "web.Request") -> "web.Response":
        """POST /webhooks/{route_name} — receive and process a webhook event."""
+        # Hot-reload dynamic subscriptions on each request (mtime-gated, cheap)
+        self._reload_dynamic_routes()
+
        route_name = request.match_info.get("route_name", "")
        route_config = self._routes.get(route_name)

@@ -26,6 +26,7 @@ from pathlib import Path
 from typing import Dict, Optional, Any

 from hermes_cli.config import get_hermes_home
+from hermes_constants import get_hermes_dir

 logger = logging.getLogger(__name__)

@@ -134,7 +135,7 @@ class WhatsAppAdapter(BasePlatformAdapter):
        )
        self._session_path: Path = Path(config.extra.get(
            "session_path",
-            get_hermes_home() / "whatsapp" / "session"
+            get_hermes_dir("platforms/whatsapp/session", "whatsapp/session")
        ))
        self._reply_prefix: Optional[str] = config.extra.get("reply_prefix")
        self._message_queue: asyncio.Queue = asyncio.Queue()
@@ -526,6 +527,7 @@ class WhatsAppAdapter(BasePlatformAdapter):
        image_path: str,
        caption: Optional[str] = None,
        reply_to: Optional[str] = None,
+        **kwargs,
    ) -> SendResult:
        """Send a local image file natively via bridge."""
        return await self._send_media_to_bridge(chat_id, image_path, "image", caption)
@@ -536,6 +538,7 @@ class WhatsAppAdapter(BasePlatformAdapter):
        video_path: str,
        caption: Optional[str] = None,
        reply_to: Optional[str] = None,
+        **kwargs,
    ) -> SendResult:
        """Send a video natively via bridge — plays inline in WhatsApp."""
        return await self._send_media_to_bridge(chat_id, video_path, "video", caption)
@@ -547,6 +550,7 @@ class WhatsAppAdapter(BasePlatformAdapter):
        caption: Optional[str] = None,
        file_name: Optional[str] = None,
        reply_to: Optional[str] = None,
+        **kwargs,
    ) -> SendResult:
        """Send a document/file as a downloadable attachment via bridge."""
        return await self._send_media_to_bridge(
@@ -288,7 +288,7 @@ def _resolve_gateway_model(config: dict | None = None) -> str:
    if isinstance(model_cfg, str):
        model = model_cfg
    elif isinstance(model_cfg, dict):
-        model = model_cfg.get("default", model)
+        model = model_cfg.get("default") or model_cfg.get("model") or model
    return model


@@ -432,7 +432,7 @@ class GatewayRunner:
            from honcho_integration.session import HonchoSessionManager

            hcfg = HonchoClientConfig.from_global_config()
-            if not hcfg.enabled or not hcfg.api_key:
+            if not hcfg.enabled or not (hcfg.api_key or hcfg.base_url):
                return None, hcfg

            client = get_honcho_client(hcfg)
@@ -573,6 +573,10 @@ class GatewayRunner:
                session_id=old_session_id,
                honcho_session_key=honcho_session_key,
            )
+            # Fully silence the flush agent — quiet_mode only suppresses init
+            # messages; tool call output still leaks to the terminal through
+            # _safe_print → _print_fn.  Set a no-op to prevent that.
+            tmp_agent._print_fn = lambda *a, **kw: None

            # Build conversation history from transcript
            msgs = [
@@ -741,10 +745,22 @@ class GatewayRunner:
                logger.error("No connected messaging platforms remain. Shutting down gateway cleanly.")
            await self.stop()
        elif not self.adapters and self._failed_platforms:
-            logger.warning(
-                "No connected messaging platforms remain, but %d platform(s) queued for reconnection",
-                len(self._failed_platforms),
-            )
+            # All platforms are down and queued for background reconnection.
+            # If the error is retryable, exit with failure so systemd Restart=on-failure
+            # can restart the process. Otherwise stay alive and keep retrying in background.
+            if adapter.fatal_error_retryable:
+                self._exit_reason = adapter.fatal_error_message or "All messaging platforms failed with retryable errors"
+                self._exit_with_failure = True
+                logger.error(
+                    "All messaging platforms failed with retryable errors. "
+                    "Shutting down gateway for service restart (systemd will retry)."
+                )
+                await self.stop()
+            else:
+                logger.warning(
+                    "No connected messaging platforms remain, but %d platform(s) queued for reconnection",
+                    len(self._failed_platforms),
+                )

    def _request_clean_exit(self, reason: str) -> None:
        self._exit_cleanly = True
@@ -954,12 +970,20 @@ class GatewayRunner:
            os.getenv(v)
            for v in ("TELEGRAM_ALLOWED_USERS", "DISCORD_ALLOWED_USERS",
                       "WHATSAPP_ALLOWED_USERS", "SLACK_ALLOWED_USERS",
-                       "SIGNAL_ALLOWED_USERS", "EMAIL_ALLOWED_USERS",
+                       "SIGNAL_ALLOWED_USERS", "SIGNAL_GROUP_ALLOWED_USERS",
+                       "EMAIL_ALLOWED_USERS",
                       "SMS_ALLOWED_USERS", "MATTERMOST_ALLOWED_USERS",
                       "MATRIX_ALLOWED_USERS", "DINGTALK_ALLOWED_USERS",
                       "GATEWAY_ALLOWED_USERS")
        )
-        _allow_all = os.getenv("GATEWAY_ALLOW_ALL_USERS", "").lower() in ("true", "1", "yes")
+        _allow_all = os.getenv("GATEWAY_ALLOW_ALL_USERS", "").lower() in ("true", "1", "yes") or any(
+            os.getenv(v, "").lower() in ("true", "1", "yes")
+            for v in ("TELEGRAM_ALLOW_ALL_USERS", "DISCORD_ALLOW_ALL_USERS",
+                       "WHATSAPP_ALLOW_ALL_USERS", "SLACK_ALLOW_ALL_USERS",
+                       "SIGNAL_ALLOW_ALL_USERS", "EMAIL_ALLOW_ALL_USERS",
+                       "SMS_ALLOW_ALL_USERS", "MATTERMOST_ALLOW_ALL_USERS",
+                       "MATRIX_ALLOW_ALL_USERS", "DINGTALK_ALLOW_ALL_USERS")
+        )
        if not _any_allowlist and not _allow_all:
            logger.warning(
                "No user allowlists configured. All unauthorized users will be denied. "
@@ -1970,6 +1994,12 @@ class GatewayRunner:
                            f"Use /resume to browse and restore a previous session.\n"
                            f"Adjust reset timing in config.yaml under session_reset."
                        )
+                        try:
+                            session_info = self._format_session_info()
+                            if session_info:
+                                notice = f"{notice}\n\n{session_info}"
+                        except Exception:
+                            pass
                        await adapter.send(
                            source.chat_id, notice,
                            metadata=getattr(event, 'metadata', None),
@@ -2063,7 +2093,7 @@ class GatewayRunner:
                    if isinstance(_model_cfg, str):
                        _hyg_model = _model_cfg
                    elif isinstance(_model_cfg, dict):
-                        _hyg_model = _model_cfg.get("default", _hyg_model)
+                        _hyg_model = _model_cfg.get("default") or _model_cfg.get("model") or _hyg_model
                        # Read explicit context_length override from model config
                        # (same as run_agent.py lines 995-1005)
                        _raw_ctx = _model_cfg.get("context_length")
@@ -2175,6 +2205,7 @@ class GatewayRunner:
                                    enabled_toolsets=["memory"],
                                    session_id=session_entry.session_id,
                                )
+                                _hyg_agent._print_fn = lambda *a, **kw: None

                                loop = asyncio.get_event_loop()
                                _compressed, _ = await loop.run_in_executor(
@@ -2185,6 +2216,15 @@ class GatewayRunner:
                                    ),
                                )

+                                # _compress_context ends the old session and creates
+                                # a new session_id.  Write compressed messages into
+                                # the NEW session so the old transcript stays intact
+                                # and searchable via session_search.
+                                _hyg_new_sid = _hyg_agent.session_id
+                                if _hyg_new_sid != session_entry.session_id:
+                                    session_entry.session_id = _hyg_new_sid
+                                    self.session_store._save()
+
                                self.session_store.rewrite_transcript(
                                    session_entry.session_id, _compressed
                                )
@@ -2736,6 +2776,85 @@ class GatewayRunner:
            # Clear session env
            self._clear_session_env()
    
+    def _format_session_info(self) -> str:
+        """Resolve current model config and return a formatted info block.
+
+        Surfaces model, provider, context length, and endpoint so gateway
+        users can immediately see if context detection went wrong (e.g.
+        local models falling to the 128K default).
+        """
+        from agent.model_metadata import get_model_context_length, DEFAULT_FALLBACK_CONTEXT
+
+        model = _resolve_gateway_model()
+        config_context_length = None
+        provider = None
+        base_url = None
+        api_key = None
+
+        try:
+            cfg_path = _hermes_home / "config.yaml"
+            if cfg_path.exists():
+                import yaml as _info_yaml
+                with open(cfg_path, encoding="utf-8") as f:
+                    data = _info_yaml.safe_load(f) or {}
+                model_cfg = data.get("model", {})
+                if isinstance(model_cfg, dict):
+                    raw_ctx = model_cfg.get("context_length")
+                    if raw_ctx is not None:
+                        try:
+                            config_context_length = int(raw_ctx)
+                        except (TypeError, ValueError):
+                            pass
+                    provider = model_cfg.get("provider") or None
+                    base_url = model_cfg.get("base_url") or None
+        except Exception:
+            pass
+
+        # Resolve runtime credentials for probing
+        try:
+            runtime = _resolve_runtime_agent_kwargs()
+            provider = provider or runtime.get("provider")
+            base_url = base_url or runtime.get("base_url")
+            api_key = runtime.get("api_key")
+        except Exception:
+            pass
+
+        context_length = get_model_context_length(
+            model,
+            base_url=base_url or "",
+            api_key=api_key or "",
+            config_context_length=config_context_length,
+            provider=provider or "",
+        )
+
+        # Format context source hint
+        if config_context_length is not None:
+            ctx_source = "config"
+        elif context_length == DEFAULT_FALLBACK_CONTEXT:
+            ctx_source = "default — set model.context_length in config to override"
+        else:
+            ctx_source = "detected"
+
+        # Format context length for display
+        if context_length >= 1_000_000:
+            ctx_display = f"{context_length / 1_000_000:.1f}M"
+        elif context_length >= 1_000:
+            ctx_display = f"{context_length // 1_000}K"
+        else:
+            ctx_display = str(context_length)
+
+        lines = [
+            f"◆ Model: `{model}`",
+            f"◆ Provider: {provider or 'openrouter'}",
+            f"◆ Context: {ctx_display} tokens ({ctx_source})",
+        ]
+
+        # Show endpoint for local/custom setups
+        if base_url and ("localhost" in base_url or "127.0.0.1" in base_url or "0.0.0.0" in base_url):
+            lines.append(f"◆ Endpoint: {base_url}")
+
+        return "\n".join(lines)
+
    async def _handle_reset_command(self, event: MessageEvent) -> str:
        """Handle /new or /reset command."""
        source = event.source
@@ -2776,12 +2895,22 @@ class GatewayRunner:
            "session_key": session_key,
        })
        
+        # Resolve session config info to surface to the user
+        try:
+            session_info = self._format_session_info()
+        except Exception:
+            session_info = ""
+
        if new_entry:
-            return "✨ Session reset! I've started fresh with no memory of our previous conversation."
+            header = "✨ Session reset! Starting fresh."
        else:
            # No existing session, just create one
            self.session_store.get_or_create_session(source, force_new=True)
-            return "✨ New session started!"
+            header = "✨ New session started!"
+
+        if session_info:
+            return f"{header}\n\n{session_info}"
+        return header
    
    async def _handle_status_command(self, event: MessageEvent) -> str:
        """Handle /status command."""
@@ -3885,17 +4014,27 @@ class GatewayRunner:
                enabled_toolsets=["memory"],
                session_id=session_entry.session_id,
            )
+            tmp_agent._print_fn = lambda *a, **kw: None

            loop = asyncio.get_event_loop()
            compressed, _ = await loop.run_in_executor(
                None,
-                lambda: tmp_agent._compress_context(msgs, "", approx_tokens=approx_tokens),
+                lambda: tmp_agent._compress_context(msgs, "", approx_tokens=approx_tokens)
            )

-            self.session_store.rewrite_transcript(session_entry.session_id, compressed)
+            # _compress_context already calls end_session() on the old session
+            # (preserving its full transcript in SQLite) and creates a new
+            # session_id for the continuation.  Write the compressed messages
+            # into the NEW session so the original history stays searchable.
+            new_session_id = tmp_agent.session_id
+            if new_session_id != session_entry.session_id:
+                session_entry.session_id = new_session_id
+                self.session_store._save()
+
+            self.session_store.rewrite_transcript(new_session_id, compressed)
            # Reset stored token count — transcript changed, old value is stale
            self.session_store.update_session(
-                session_entry.session_key, last_prompt_tokens=0,
+                session_entry.session_key, last_prompt_tokens=0
            )
            new_count = len(compressed)
            new_tokens = estimate_messages_tokens_rough(compressed)
@@ -4051,7 +4190,7 @@ class GatewayRunner:
            ]
            ctx = agent.context_compressor
            if ctx.last_prompt_tokens:
-                pct = ctx.last_prompt_tokens / ctx.context_length * 100 if ctx.context_length else 0
+                pct = min(100, ctx.last_prompt_tokens / ctx.context_length * 100) if ctx.context_length else 0
                lines.append(f"Context: {ctx.last_prompt_tokens:,} / {ctx.context_length:,} ({pct:.0f}%)")
            if ctx.compression_count:
                lines.append(f"Compressions: {ctx.compression_count}")
@@ -4799,9 +4938,14 @@ class GatewayRunner:
        enabled_toolsets = sorted(_get_platform_tools(user_config, platform_key))

        # Tool progress mode from config.yaml: "all", "new", "verbose", "off"
-        # Falls back to env vars for backward compatibility
+        # Falls back to env vars for backward compatibility.
+        # YAML 1.1 parses bare `off` as boolean False — normalise before
+        # the `or` chain so it doesn't silently fall through to "all".
+        _raw_tp = user_config.get("display", {}).get("tool_progress")
+        if _raw_tp is False:
+            _raw_tp = "off"
        progress_mode = (
-            user_config.get("display", {}).get("tool_progress")
+            _raw_tp
            or os.getenv("HERMES_TOOL_PROGRESS_MODE")
            or "all"
        )
@@ -4860,12 +5004,17 @@ class GatewayRunner:
            progress_queue.put(msg)
        
        # Background task to send progress messages
-        # Accumulates tool lines into a single message that gets edited
-        # For DM top-level Slack messages, source.thread_id is None but the
-        # final reply will be threaded under the original message via reply_to.
-        # Use event_message_id as fallback so progress messages land in the
-        # same thread as the final response instead of going to the DM root.
-        _progress_thread_id = source.thread_id or event_message_id
+        # Accumulates tool lines into a single message that gets edited.
+        #
+        # Threading metadata is platform-specific:
+        # - Slack DM threading needs event_message_id fallback (reply thread)
+        # - Telegram uses message_thread_id only for forum topics; passing a
+        #   normal DM/group message id as thread_id causes send failures
+        # - Other platforms should use explicit source.thread_id only
+        if source.platform == Platform.SLACK:
+            _progress_thread_id = source.thread_id or event_message_id
+        else:
+            _progress_thread_id = source.thread_id
        _progress_metadata = {"thread_id": _progress_thread_id} if _progress_thread_id else None

        async def send_progress_messages():
@@ -5128,7 +5277,25 @@ class GatewayRunner:
            agent.stream_delta_callback = _stream_delta_cb
            agent.status_callback = _status_callback_sync
            agent.reasoning_config = reasoning_config
-            
+
+            # Background review delivery — send "💾 Memory updated" etc. to user
+            def _bg_review_send(message: str) -> None:
+                if not _status_adapter:
+                    return
+                try:
+                    asyncio.run_coroutine_threadsafe(
+                        _status_adapter.send(
+                            _status_chat_id,
+                            message,
+                            metadata=_status_thread_metadata,
+                        ),
+                        _loop_for_step,
+                    )
+                except Exception as _e:
+                    logger.debug("background_review_callback error: %s", _e)
+
+            agent.background_review_callback = _bg_review_send
+
            # Store agent reference for interrupt support
            agent_holder[0] = agent
            # Capture the full tool definitions for transcript logging
@@ -762,14 +762,16 @@ class SessionStore:
            if session_key in self._entries:
                entry = self._entries[session_key]
                entry.updated_at = _now()
-                entry.input_tokens += input_tokens
-                entry.output_tokens += output_tokens
-                entry.cache_read_tokens += cache_read_tokens
-                entry.cache_write_tokens += cache_write_tokens
+                # Direct assignment — the gateway receives cumulative totals
+                # from the cached agent, not per-call deltas.
+                entry.input_tokens = input_tokens
+                entry.output_tokens = output_tokens
+                entry.cache_read_tokens = cache_read_tokens
+                entry.cache_write_tokens = cache_write_tokens
                if last_prompt_tokens is not None:
                    entry.last_prompt_tokens = last_prompt_tokens
                if estimated_cost_usd is not None:
-                    entry.estimated_cost_usd += estimated_cost_usd
+                    entry.estimated_cost_usd = estimated_cost_usd
                if cost_status:
                    entry.cost_status = cost_status
                entry.total_tokens = (
@@ -783,7 +785,7 @@ class SessionStore:

        if self._db and db_session_id:
            try:
-                self._db.update_token_counts(
+                self._db.set_token_counts(
                    db_session_id,
                    input_tokens=input_tokens,
                    output_tokens=output_tokens,
@@ -795,6 +797,7 @@ class SessionStore:
                    billing_provider=provider,
                    billing_base_url=base_url,
                    model=model,
+                    absolute=True,
                )
            except Exception as e:
                logger.debug("Session DB operation failed: %s", e)
@@ -955,13 +958,17 @@ class SessionStore:
            try:
                self._db.clear_messages(session_id)
                for msg in messages:
+                    role = msg.get("role", "unknown")
                    self._db.append_message(
                        session_id=session_id,
-                        role=msg.get("role", "unknown"),
+                        role=role,
                        content=msg.get("content"),
                        tool_name=msg.get("tool_name"),
                        tool_calls=msg.get("tool_calls"),
                        tool_call_id=msg.get("tool_call_id"),
+                        reasoning=msg.get("reasoning") if role == "assistant" else None,
+                        reasoning_details=msg.get("reasoning_details") if role == "assistant" else None,
+                        codex_reasoning_items=msg.get("codex_reasoning_items") if role == "assistant" else None,
                    )
            except Exception as e:
                logger.debug("Failed to rewrite transcript in DB: %s", e)
@@ -11,5 +11,5 @@ Provides subcommands for:
 - hermes cron          - Manage cron jobs
 """

-__version__ = "0.4.0"
-__release_date__ = "2026.3.23"
+__version__ = "0.5.0"
+__release_date__ = "2026.3.28"
@@ -160,7 +160,7 @@ PROVIDER_REGISTRY: Dict[str, ProviderConfig] = {
        id="alibaba",
        name="Alibaba Cloud (DashScope)",
        auth_type="api_key",
-        inference_base_url="https://dashscope-intl.aliyuncs.com/apps/anthropic",
+        inference_base_url="https://coding-intl.dashscope.aliyuncs.com/v1",
        api_key_env_vars=("DASHSCOPE_API_KEY",),
        base_url_env_var="DASHSCOPE_BASE_URL",
    ),
@@ -212,6 +212,14 @@ PROVIDER_REGISTRY: Dict[str, ProviderConfig] = {
        api_key_env_vars=("KILOCODE_API_KEY",),
        base_url_env_var="KILOCODE_BASE_URL",
    ),
+    "huggingface": ProviderConfig(
+        id="huggingface",
+        name="Hugging Face",
+        auth_type="api_key",
+        inference_base_url="https://router.huggingface.co/v1",
+        api_key_env_vars=("HF_TOKEN",),
+        base_url_env_var="HF_BASE_URL",
+    ),
 }


@@ -685,6 +693,7 @@ def resolve_provider(
        "github-copilot-acp": "copilot-acp", "copilot-acp-agent": "copilot-acp",
        "aigateway": "ai-gateway", "vercel": "ai-gateway", "vercel-ai-gateway": "ai-gateway",
        "opencode": "opencode-zen", "zen": "opencode-zen",
+        "hf": "huggingface", "hugging-face": "huggingface", "huggingface-hub": "huggingface",
        "go": "opencode-go", "opencode-go-sub": "opencode-go",
        "kilo": "kilocode", "kilo-code": "kilocode", "kilo-gateway": "kilocode",
    }
@@ -138,6 +138,12 @@ DEFAULT_CONFIG = {
    "toolsets": ["hermes-cli"],
    "agent": {
        "max_turns": 90,
+        # Tool-use enforcement: injects system prompt guidance that tells the
+        # model to actually call tools instead of describing intended actions.
+        # Values: "auto" (default — applies to gpt/codex models), true/false
+        # (force on/off for all models), or a list of model-name substrings
+        # to match (e.g. ["gpt", "codex", "gemini", "qwen"]).
+        "tool_use_enforcement": "auto",
    },
    
    "terminal": {
@@ -221,42 +227,49 @@ DEFAULT_CONFIG = {
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 30,         # seconds — increase for slow local models
        },
        "compression": {
            "provider": "auto",
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 120,        # seconds — compression summarises large contexts; increase for local models
        },
        "session_search": {
            "provider": "auto",
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 30,
        },
        "skills_hub": {
            "provider": "auto",
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 30,
        },
        "approval": {
            "provider": "auto",
            "model": "",           # fast/cheap model recommended (e.g. gemini-flash, haiku)
            "base_url": "",
            "api_key": "",
+            "timeout": 30,
        },
        "mcp": {
            "provider": "auto",
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 30,
        },
        "flush_memories": {
            "provider": "auto",
            "model": "",
            "base_url": "",
            "api_key": "",
+            "timeout": 30,
        },
    },
    
@@ -264,6 +277,7 @@ DEFAULT_CONFIG = {
        "compact": False,
        "personality": "kawaii",
        "resume_display": "full",
+        "busy_input_mode": "interrupt",
        "bell_on_complete": False,
        "show_reasoning": False,
        "streaming": False,
@@ -546,14 +560,14 @@ OPTIONAL_ENV_VARS = {
        "category": "provider",
    },
    "DASHSCOPE_API_KEY": {
-        "description": "Alibaba Cloud DashScope API key for Qwen models",
+        "description": "Alibaba Cloud DashScope API key (Qwen + multi-provider models)",
        "prompt": "DashScope API Key",
        "url": "https://modelstudio.console.alibabacloud.com/",
        "password": True,
        "category": "provider",
    },
    "DASHSCOPE_BASE_URL": {
-        "description": "Custom DashScope base URL (default: international endpoint)",
+        "description": "Custom DashScope base URL (default: coding-intl OpenAI-compat endpoint)",
        "prompt": "DashScope Base URL",
        "url": "",
        "password": False,
@@ -592,8 +606,31 @@ OPTIONAL_ENV_VARS = {
        "category": "provider",
        "advanced": True,
    },
+    "HF_TOKEN": {
+        "description": "Hugging Face token for Inference Providers (20+ open models via router.huggingface.co)",
+        "prompt": "Hugging Face Token",
+        "url": "https://huggingface.co/settings/tokens",
+        "password": True,
+        "category": "provider",
+    },
+    "HF_BASE_URL": {
+        "description": "Hugging Face Inference Providers base URL override",
+        "prompt": "HF base URL (leave empty for default)",
+        "url": None,
+        "password": False,
+        "category": "provider",
+        "advanced": True,
+    },

    # ── Tool API keys ──
+    "EXA_API_KEY": {
+        "description": "Exa API key for AI-native web search and contents",
+        "prompt": "Exa API key",
+        "url": "https://exa.ai/",
+        "tools": ["web_search", "web_extract"],
+        "password": True,
+        "category": "tool",
+    },
    "PARALLEL_API_KEY": {
        "description": "Parallel API key for AI-native web search and extract",
        "prompt": "Parallel API key",
@@ -780,6 +817,20 @@ OPTIONAL_ENV_VARS = {
        "password": False,
        "category": "messaging",
    },
+    "MATTERMOST_REQUIRE_MENTION": {
+        "description": "Require @mention in Mattermost channels (default: true). Set to false to respond to all messages.",
+        "prompt": "Require @mention in channels",
+        "url": None,
+        "password": False,
+        "category": "messaging",
+    },
+    "MATTERMOST_FREE_RESPONSE_CHANNELS": {
+        "description": "Comma-separated Mattermost channel IDs where bot responds without @mention",
+        "prompt": "Free-response channel IDs (comma-separated)",
+        "url": None,
+        "password": False,
+        "category": "messaging",
+    },
    "MATRIX_HOMESERVER": {
        "description": "Matrix homeserver URL (e.g. https://matrix.example.org)",
        "prompt": "Matrix homeserver URL",
@@ -1650,6 +1701,7 @@ def show_config():
    keys = [
        ("OPENROUTER_API_KEY", "OpenRouter"),
        ("VOICE_TOOLS_OPENAI_KEY", "OpenAI (STT/TTS)"),
+        ("EXA_API_KEY", "Exa"),
        ("PARALLEL_API_KEY", "Parallel"),
        ("FIRECRAWL_API_KEY", "Firecrawl"),
        ("TAVILY_API_KEY", "Tavily"),
@@ -1809,7 +1861,7 @@ def set_config_value(key: str, value: str):
    # Check if it's an API key (goes to .env)
    api_keys = [
        'OPENROUTER_API_KEY', 'OPENAI_API_KEY', 'ANTHROPIC_API_KEY', 'VOICE_TOOLS_OPENAI_KEY',
-        'PARALLEL_API_KEY', 'FIRECRAWL_API_KEY', 'FIRECRAWL_API_URL', 'TAVILY_API_KEY',
+        'EXA_API_KEY', 'PARALLEL_API_KEY', 'FIRECRAWL_API_KEY', 'FIRECRAWL_API_URL', 'TAVILY_API_KEY',
        'BROWSERBASE_API_KEY', 'BROWSERBASE_PROJECT_ID', 'BROWSER_USE_API_KEY',
        'FAL_KEY', 'TELEGRAM_BOT_TOKEN', 'DISCORD_BOT_TOKEN',
        'TERMINAL_SSH_HOST', 'TERMINAL_SSH_USER', 'TERMINAL_SSH_KEY',
@@ -56,7 +56,7 @@ def _honcho_is_configured_for_doctor() -> bool:
        from honcho_integration.client import HonchoClientConfig

        cfg = HonchoClientConfig.from_global_config()
-        return bool(cfg.enabled and cfg.api_key)
+        return bool(cfg.enabled and (cfg.api_key or cfg.base_url))
    except Exception:
        return False

@@ -708,8 +708,8 @@ def run_doctor(args):
            check_warn("Honcho config not found", "run: hermes honcho setup")
        elif not hcfg.enabled:
            check_info(f"Honcho disabled (set enabled: true in {_honcho_cfg_path} to activate)")
-        elif not hcfg.api_key:
-            check_fail("Honcho API key not set", "run: hermes honcho setup")
+        elif not (hcfg.api_key or hcfg.base_url):
+            check_fail("Honcho API key or base URL not set", "run: hermes honcho setup")
            issues.append("No Honcho API key — run 'hermes honcho setup'")
        else:
            from honcho_integration.client import get_honcho_client, reset_honcho_client
@@ -125,20 +125,43 @@ _SERVICE_BASE = "hermes-gateway"
 SERVICE_DESCRIPTION = "Hermes Agent Gateway - Messaging Platform Integration"


+def _profile_suffix() -> str:
+    """Derive a service-name suffix from the current HERMES_HOME.
+
+    Returns ``""`` for the default ``~/.hermes``, the profile name for
+    ``~/.hermes/profiles/<name>``, or a short hash for any other custom
+    HERMES_HOME path.
+    """
+    import hashlib
+    import re
+    from pathlib import Path as _Path
+    home = get_hermes_home().resolve()
+    default = (_Path.home() / ".hermes").resolve()
+    if home == default:
+        return ""
+    # Detect ~/.hermes/profiles/<name> pattern → use the profile name
+    profiles_root = (default / "profiles").resolve()
+    try:
+        rel = home.relative_to(profiles_root)
+        parts = rel.parts
+        if len(parts) == 1 and re.match(r"^[a-z0-9][a-z0-9_-]{0,63}$", parts[0]):
+            return parts[0]
+    except ValueError:
+        pass
+    # Fallback: short hash for arbitrary HERMES_HOME paths
+    return hashlib.sha256(str(home).encode()).hexdigest()[:8]
+
+
 def get_service_name() -> str:
    """Derive a systemd service name scoped to this HERMES_HOME.

    Default ``~/.hermes`` returns ``hermes-gateway`` (backward compatible).
-    Any other HERMES_HOME appends a short hash so multiple installations
-    can each have their own systemd service without conflicting.
+    Profile ``~/.hermes/profiles/coder`` returns ``hermes-gateway-coder``.
+    Any other HERMES_HOME appends a short hash for uniqueness.
    """
-    import hashlib
-    from pathlib import Path as _Path  # local import to avoid monkeypatch interference
-    home = get_hermes_home().resolve()
-    default = (_Path.home() / ".hermes").resolve()
-    if home == default:
+    suffix = _profile_suffix()
+    if not suffix:
        return _SERVICE_BASE
-    suffix = hashlib.sha256(str(home).encode()).hexdigest()[:8]
    return f"{_SERVICE_BASE}-{suffix}"


@@ -369,7 +392,14 @@ def print_systemd_linger_guidance() -> None:
        print("  sudo loginctl enable-linger $USER")

 def get_launchd_plist_path() -> Path:
-    return Path.home() / "Library" / "LaunchAgents" / "ai.hermes.gateway.plist"
+    """Return the launchd plist path, scoped per profile.
+
+    Default ``~/.hermes`` → ``ai.hermes.gateway.plist`` (backward compatible).
+    Profile ``~/.hermes/profiles/coder`` → ``ai.hermes.gateway-coder.plist``.
+    """
+    suffix = _profile_suffix()
+    name = f"ai.hermes.gateway-{suffix}" if suffix else "ai.hermes.gateway"
+    return Path.home() / "Library" / "LaunchAgents" / f"{name}.plist"

 def _detect_venv_dir() -> Path | None:
    """Detect the active virtualenv directory.
@@ -420,6 +450,17 @@ def get_hermes_cli_path() -> str:
 # Systemd (Linux)
 # =============================================================================

+def _build_user_local_paths(home: Path, path_entries: list[str]) -> list[str]:
+    """Return user-local bin dirs that exist and aren't already in *path_entries*."""
+    candidates = [
+        str(home / ".local" / "bin"),       # uv, uvx, pip-installed CLIs
+        str(home / ".cargo" / "bin"),        # Rust/cargo tools
+        str(home / "go" / "bin"),            # Go tools
+        str(home / ".npm-global" / "bin"),   # npm global packages
+    ]
+    return [p for p in candidates if p not in path_entries and Path(p).exists()]
+
+
 def generate_systemd_unit(system: bool = False, run_as_user: str | None = None) -> str:
    python_path = get_python_path()
    working_dir = str(PROJECT_ROOT)
@@ -434,13 +475,16 @@ def generate_systemd_unit(system: bool = False, run_as_user: str | None = None)
        resolved_node_dir = str(Path(resolved_node).resolve().parent)
        if resolved_node_dir not in path_entries:
            path_entries.append(resolved_node_dir)
-    path_entries.extend(["/usr/local/sbin", "/usr/local/bin", "/usr/sbin", "/usr/bin", "/sbin", "/bin"])
-    sane_path = ":".join(path_entries)

    hermes_home = str(get_hermes_home().resolve())

+    common_bin_paths = ["/usr/local/sbin", "/usr/local/bin", "/usr/sbin", "/usr/bin", "/sbin", "/bin"]
+
    if system:
        username, group_name, home_dir = _system_service_identity(run_as_user)
+        path_entries.extend(_build_user_local_paths(Path(home_dir), path_entries))
+        path_entries.extend(common_bin_paths)
+        sane_path = ":".join(path_entries)
        return f"""[Unit]
 Description={SERVICE_DESCRIPTION}
 After=network-online.target
@@ -472,6 +516,9 @@ StandardError=journal
 WantedBy=multi-user.target
 """

+    path_entries.extend(_build_user_local_paths(Path.home(), path_entries))
+    path_entries.extend(common_bin_paths)
+    sane_path = ":".join(path_entries)
    return f"""[Unit]
 Description={SERVICE_DESCRIPTION}
 After=network.target
@@ -752,18 +799,46 @@ def systemd_status(deep: bool = False, system: bool = False):
 # Launchd (macOS)
 # =============================================================================

+def get_launchd_label() -> str:
+    """Return the launchd service label, scoped per profile."""
+    suffix = _profile_suffix()
+    return f"ai.hermes.gateway-{suffix}" if suffix else "ai.hermes.gateway"
+
+
 def generate_launchd_plist() -> str:
    python_path = get_python_path()
    working_dir = str(PROJECT_ROOT)
+    hermes_home = str(get_hermes_home().resolve())
    log_dir = get_hermes_home() / "logs"
    log_dir.mkdir(parents=True, exist_ok=True)
-    
+    label = get_launchd_label()
+    # Build a sane PATH for the launchd plist.  launchd provides only a
+    # minimal default (/usr/bin:/bin:/usr/sbin:/sbin) which misses Homebrew,
+    # nvm, cargo, etc.  We prepend venv/bin and node_modules/.bin (matching
+    # the systemd unit), then capture the user's full shell PATH so every
+    # user-installed tool (node, ffmpeg, …) is reachable.
+    detected_venv = _detect_venv_dir()
+    venv_bin = str(detected_venv / "bin") if detected_venv else str(PROJECT_ROOT / "venv" / "bin")
+    venv_dir = str(detected_venv) if detected_venv else str(PROJECT_ROOT / "venv")
+    node_bin = str(PROJECT_ROOT / "node_modules" / ".bin")
+    # Resolve the directory containing the node binary (e.g. Homebrew, nvm)
+    # so it's explicitly in PATH even if the user's shell PATH changes later.
+    priority_dirs = [venv_bin, node_bin]
+    resolved_node = shutil.which("node")
+    if resolved_node:
+        resolved_node_dir = str(Path(resolved_node).resolve().parent)
+        if resolved_node_dir not in priority_dirs:
+            priority_dirs.append(resolved_node_dir)
+    sane_path = ":".join(
+        dict.fromkeys(priority_dirs + [p for p in os.environ.get("PATH", "").split(":") if p])
+    )
+
    return f"""<?xml version="1.0" encoding="UTF-8"?>
 <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
 <plist version="1.0">
 <dict>
    <key>Label</key>
-    <string>ai.hermes.gateway</string>
+    <string>{label}</string>
    
    <key>ProgramArguments</key>
    <array>
@@ -778,6 +853,16 @@ def generate_launchd_plist() -> str:
    <key>WorkingDirectory</key>
    <string>{working_dir}</string>
    
+    <key>EnvironmentVariables</key>
+    <dict>
+        <key>PATH</key>
+        <string>{sane_path}</string>
+        <key>VIRTUAL_ENV</key>
+        <string>{venv_dir}</string>
+        <key>HERMES_HOME</key>
+        <string>{hermes_home}</string>
+    </dict>
+    
    <key>RunAtLoad</key>
    <true/>
    
@@ -863,20 +948,33 @@ def launchd_uninstall():
    print("✓ Service uninstalled")

 def launchd_start():
-    refresh_launchd_plist_if_needed()
    plist_path = get_launchd_plist_path()
+    label = get_launchd_label()
+
+    # Self-heal if the plist is missing entirely (e.g., manual cleanup, failed upgrade)
+    if not plist_path.exists():
+        print("↻ launchd plist missing; regenerating service definition")
+        plist_path.parent.mkdir(parents=True, exist_ok=True)
+        plist_path.write_text(generate_launchd_plist(), encoding="utf-8")
+        subprocess.run(["launchctl", "load", str(plist_path)], check=True)
+        subprocess.run(["launchctl", "start", label], check=True)
+        print("✓ Service started")
+        return
+
+    refresh_launchd_plist_if_needed()
    try:
-        subprocess.run(["launchctl", "start", "ai.hermes.gateway"], check=True)
+        subprocess.run(["launchctl", "start", label], check=True)
    except subprocess.CalledProcessError as e:
-        if e.returncode != 3 or not plist_path.exists():
+        if e.returncode != 3:
            raise
        print("↻ launchd job was unloaded; reloading service definition")
        subprocess.run(["launchctl", "load", str(plist_path)], check=True)
-        subprocess.run(["launchctl", "start", "ai.hermes.gateway"], check=True)
+        subprocess.run(["launchctl", "start", label], check=True)
    print("✓ Service started")

 def launchd_stop():
-    subprocess.run(["launchctl", "stop", "ai.hermes.gateway"], check=True)
+    label = get_launchd_label()
+    subprocess.run(["launchctl", "stop", label], check=True)
    print("✓ Service stopped")

 def _wait_for_gateway_exit(timeout: float = 10.0, force_after: float = 5.0):
@@ -931,8 +1029,9 @@ def launchd_restart():

 def launchd_status(deep: bool = False):
    plist_path = get_launchd_plist_path()
+    label = get_launchd_label()
    result = subprocess.run(
-        ["launchctl", "list", "ai.hermes.gateway"],
+        ["launchctl", "list", label],
        capture_output=True,
        text=True
    )
@@ -1437,7 +1536,7 @@ def _is_service_running() -> bool:
        return False
    elif is_macos() and get_launchd_plist_path().exists():
        result = subprocess.run(
-            ["launchctl", "list", "ai.hermes.gateway"],
+            ["launchctl", "list", get_launchd_label()],
            capture_output=True, text=True
        )
        return result.returncode == 0
@@ -795,6 +795,7 @@ def cmd_model(args):
        "ai-gateway": "AI Gateway",
        "kilocode": "Kilo Code",
        "alibaba": "Alibaba Cloud (DashScope)",
+        "huggingface": "Hugging Face",
        "custom": "Custom endpoint",
    }
    active_label = provider_labels.get(active, active)
@@ -820,7 +821,8 @@ def cmd_model(args):
        ("opencode-zen", "OpenCode Zen (35+ curated models, pay-as-you-go)"),
        ("opencode-go", "OpenCode Go (open models, $10/month subscription)"),
        ("ai-gateway", "AI Gateway (Vercel — 200+ models, pay-per-use)"),
-        ("alibaba", "Alibaba Cloud / DashScope (Qwen models, Anthropic-compatible)"),
+        ("alibaba", "Alibaba Cloud / DashScope Coding (Qwen + multi-provider)"),
+        ("huggingface", "Hugging Face Inference Providers (20+ open models)"),
    ]

    # Add user-defined custom providers from config.yaml
@@ -830,8 +832,8 @@ def cmd_model(args):
        for entry in custom_providers_cfg:
            if not isinstance(entry, dict):
                continue
-            name = entry.get("name", "").strip()
-            base_url = entry.get("base_url", "").strip()
+            name = (entry.get("name") or "").strip()
+            base_url = (entry.get("base_url") or "").strip()
            if not name or not base_url:
                continue
            # Generate a stable key from the name
@@ -893,7 +895,7 @@ def cmd_model(args):
        _model_flow_anthropic(config, current_model)
    elif selected_provider == "kimi-coding":
        _model_flow_kimi(config, current_model)
-    elif selected_provider in ("zai", "minimax", "minimax-cn", "kilocode", "opencode-zen", "opencode-go", "ai-gateway", "alibaba"):
+    elif selected_provider in ("zai", "minimax", "minimax-cn", "kilocode", "opencode-zen", "opencode-go", "ai-gateway", "alibaba", "huggingface"):
        _model_flow_api_key_provider(config, selected_provider, current_model)


@@ -1502,6 +1504,18 @@ _PROVIDER_MODELS = {
        "google/gemini-3-pro-preview",
        "google/gemini-3-flash-preview",
    ],
+    # Curated HF model list — only agentic models that map to OpenRouter defaults.
+    # Format: HF model ID → OpenRouter equivalent noted in comment
+    "huggingface": [
+        "Qwen/Qwen3.5-397B-A17B",                  # ↔ qwen/qwen3.5-plus
+        "Qwen/Qwen3.5-35B-A3B",                     # ↔ qwen/qwen3.5-35b-a3b
+        "deepseek-ai/DeepSeek-V3.2",                # ↔ deepseek/deepseek-chat
+        "moonshotai/Kimi-K2.5",                      # ↔ moonshotai/kimi-k2.5
+        "MiniMaxAI/MiniMax-M2.5",                    # ↔ minimax/minimax-m2.5
+        "zai-org/GLM-5",                             # ↔ z-ai/glm-5
+        "XiaomiMiMo/MiMo-V2-Flash",                 # ↔ xiaomi/mimo-v2-pro
+        "moonshotai/Kimi-K2-Thinking",               # ↔ moonshotai/kimi-k2-thinking
+    ],
 }


@@ -2031,19 +2045,25 @@ def _model_flow_api_key_provider(config, provider_id, current_model=""):
        save_env_value(base_url_env, override)
        effective_base = override

-    # Model selection — try live /models endpoint first, fall back to defaults
-    from hermes_cli.models import fetch_api_models
-    api_key_for_probe = existing_key or (get_env_value(key_env) if key_env else "")
-    live_models = fetch_api_models(api_key_for_probe, effective_base)
+    # Model selection — try live /models endpoint first, fall back to defaults.
+    # Providers with large live catalogs (100+ models) use a curated list instead
+    # so users see familiar model names rather than an overwhelming dump.
+    curated = _PROVIDER_MODELS.get(provider_id, [])
+    if curated and len(curated) >= 8:
+        # Curated list is substantial — use it directly, skip live probe
+        live_models = None
+    else:
+        from hermes_cli.models import fetch_api_models
+        api_key_for_probe = existing_key or (get_env_value(key_env) if key_env else "")
+        live_models = fetch_api_models(api_key_for_probe, effective_base)

    if live_models:
        model_list = live_models
        print(f"  Found {len(model_list)} model(s) from {pconfig.name} API")
    else:
-        model_list = _PROVIDER_MODELS.get(provider_id, [])
+        model_list = curated
        if model_list:
-            print("  ⚠ Could not auto-detect models from API — showing defaults.")
-            print("    Use \"Enter custom model name\" if you don't see your model.")
+            print(f"  Showing {len(model_list)} curated models — use \"Enter custom model name\" for others.")
        # else: no defaults either, will fall through to raw input

    if model_list:
@@ -2319,6 +2339,12 @@ def cmd_cron(args):
    cron_command(args)


+def cmd_webhook(args):
+    """Webhook subscription management."""
+    from hermes_cli.webhook import webhook_command
+    webhook_command(args)
+
+
 def cmd_doctor(args):
    """Check configuration and dependencies."""
    from hermes_cli.doctor import run_doctor
@@ -2450,8 +2476,18 @@ def _update_via_zip(args):
            )
    else:
        # Use sys.executable to explicitly call the venv's pip module,
-        # avoiding PEP 668 'externally-managed-environment' errors on Debian/Ubuntu
+        # avoiding PEP 668 'externally-managed-environment' errors on Debian/Ubuntu.
+        # Some environments lose pip inside the venv; bootstrap it back with
+        # ensurepip before trying the editable install.
        pip_cmd = [sys.executable, "-m", "pip"]
+        try:
+            subprocess.run(pip_cmd + ["--version"], cwd=PROJECT_ROOT, check=True, capture_output=True)
+        except subprocess.CalledProcessError:
+            subprocess.run(
+                [sys.executable, "-m", "ensurepip", "--upgrade", "--default-pip"],
+                cwd=PROJECT_ROOT,
+                check=True,
+            )
        try:
            subprocess.run(pip_cmd + ["install", "-e", ".[all]", "--quiet"], cwd=PROJECT_ROOT, check=True)
        except subprocess.CalledProcessError:
@@ -2612,7 +2648,12 @@ def _restore_stashed_changes(
            print("Resolve conflicts manually, then run: git stash drop")

        print(f"Restore your changes with: git stash apply {stash_ref}")
-        sys.exit(1)
+        # In non-interactive mode (gateway /update), don't abort — the code
+        # update itself succeeded, only the stash restore had conflicts.
+        # Aborting would report the entire update as failed.
+        if prompt_user:
+            sys.exit(1)
+        return False

    stash_selector = _resolve_stash_selector(git_cmd, cwd, stash_ref)
    if stash_selector is None:
@@ -2686,30 +2727,60 @@ def cmd_update(args):

    # Fetch and pull
    try:
-        print("→ Fetching updates...")
        git_cmd = ["git"]
        if sys.platform == "win32":
            git_cmd = ["git", "-c", "windows.appendAtomically=false"]
-        
-        subprocess.run(git_cmd + ["fetch", "origin"], cwd=PROJECT_ROOT, check=True)
-        
-        # Get current branch
+
+        print("→ Fetching updates...")
+        fetch_result = subprocess.run(
+            git_cmd + ["fetch", "origin"],
+            cwd=PROJECT_ROOT,
+            capture_output=True,
+            text=True,
+        )
+        if fetch_result.returncode != 0:
+            stderr = fetch_result.stderr.strip()
+            if "Could not resolve host" in stderr or "unable to access" in stderr:
+                print("✗ Network error — cannot reach the remote repository.")
+                print(f"  {stderr.splitlines()[0]}" if stderr else "")
+            elif "Authentication failed" in stderr or "could not read Username" in stderr:
+                print("✗ Authentication failed — check your git credentials or SSH key.")
+            else:
+                print(f"✗ Failed to fetch updates from origin.")
+                if stderr:
+                    print(f"  {stderr.splitlines()[0]}")
+            sys.exit(1)
+
+        # Get current branch (returns literal "HEAD" when detached)
        result = subprocess.run(
            git_cmd + ["rev-parse", "--abbrev-ref", "HEAD"],
            cwd=PROJECT_ROOT,
            capture_output=True,
            text=True,
-            check=True
+            check=True,
        )
-        branch = result.stdout.strip()
+        current_branch = result.stdout.strip()

-        # Fall back to main if the current branch doesn't exist on the remote
-        verify = subprocess.run(
-            git_cmd + ["rev-parse", "--verify", f"origin/{branch}"],
-            cwd=PROJECT_ROOT, capture_output=True, text=True,
-        )
-        if verify.returncode != 0:
-            branch = "main"
+        # Always update against main
+        branch = "main"
+
+        # If user is on a non-main branch or detached HEAD, switch to main
+        if current_branch != "main":
+            label = "detached HEAD" if current_branch == "HEAD" else f"branch '{current_branch}'"
+            print(f"  ⚠ Currently on {label} — switching to main for update...")
+            # Stash before checkout so uncommitted work isn't lost
+            auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
+            subprocess.run(
+                git_cmd + ["checkout", "main"],
+                cwd=PROJECT_ROOT,
+                capture_output=True,
+                text=True,
+                check=True,
+            )
+        else:
+            auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
+
+        prompt_for_restore = auto_stash_ref is not None and sys.stdin.isatty() and sys.stdout.isatty()

        # Check if there are updates
        result = subprocess.run(
@@ -2717,31 +2788,69 @@ def cmd_update(args):
            cwd=PROJECT_ROOT,
            capture_output=True,
            text=True,
-            check=True
+            check=True,
        )
        commit_count = int(result.stdout.strip())
-        
+
        if commit_count == 0:
            _invalidate_update_cache()
-            print("✓ Already up to date!")
-            return
-        
-        print(f"→ Found {commit_count} new commit(s)")
-
-        auto_stash_ref = _stash_local_changes_if_needed(git_cmd, PROJECT_ROOT)
-        prompt_for_restore = auto_stash_ref is not None and sys.stdin.isatty() and sys.stdout.isatty()
-
-        print("→ Pulling updates...")
-        try:
-            subprocess.run(git_cmd + ["pull", "--ff-only", "origin", branch], cwd=PROJECT_ROOT, check=True)
-        finally:
+            # Restore stash and switch back to original branch if we moved
            if auto_stash_ref is not None:
                _restore_stashed_changes(
-                    git_cmd,
-                    PROJECT_ROOT,
-                    auto_stash_ref,
+                    git_cmd, PROJECT_ROOT, auto_stash_ref,
                    prompt_user=prompt_for_restore,
                )
+            if current_branch not in ("main", "HEAD"):
+                subprocess.run(
+                    git_cmd + ["checkout", current_branch],
+                    cwd=PROJECT_ROOT, capture_output=True, text=True, check=False,
+                )
+            print("✓ Already up to date!")
+            return
+
+        print(f"→ Found {commit_count} new commit(s)")
+
+        print("→ Pulling updates...")
+        update_succeeded = False
+        try:
+            pull_result = subprocess.run(
+                git_cmd + ["pull", "--ff-only", "origin", branch],
+                cwd=PROJECT_ROOT,
+                capture_output=True,
+                text=True,
+            )
+            if pull_result.returncode != 0:
+                # ff-only failed — local and remote have diverged (e.g. upstream
+                # force-pushed or rebase).  Since local changes are already
+                # stashed, reset to match the remote exactly.
+                print("  ⚠ Fast-forward not possible (history diverged), resetting to match remote...")
+                reset_result = subprocess.run(
+                    git_cmd + ["reset", "--hard", f"origin/{branch}"],
+                    cwd=PROJECT_ROOT,
+                    capture_output=True,
+                    text=True,
+                )
+                if reset_result.returncode != 0:
+                    print(f"✗ Failed to reset to origin/{branch}.")
+                    if reset_result.stderr.strip():
+                        print(f"  {reset_result.stderr.strip()}")
+                    print("  Try manually: git fetch origin && git reset --hard origin/main")
+                    sys.exit(1)
+            update_succeeded = True
+        finally:
+            if auto_stash_ref is not None:
+                # Don't attempt stash restore if the code update itself failed —
+                # working tree is in an unknown state.
+                if not update_succeeded:
+                    print(f"  ℹ️  Local changes preserved in stash (ref: {auto_stash_ref})")
+                    print(f"  Restore manually with: git stash apply")
+                else:
+                    _restore_stashed_changes(
+                        git_cmd,
+                        PROJECT_ROOT,
+                        auto_stash_ref,
+                        prompt_user=prompt_for_restore,
+                    )
        
        _invalidate_update_cache()
        
@@ -2764,8 +2873,18 @@ def cmd_update(args):
                )
        else:
            # Use sys.executable to explicitly call the venv's pip module,
-            # avoiding PEP 668 'externally-managed-environment' errors on Debian/Ubuntu
+            # avoiding PEP 668 'externally-managed-environment' errors on Debian/Ubuntu.
+            # Some environments lose pip inside the venv; bootstrap it back with
+            # ensurepip before trying the editable install.
            pip_cmd = [sys.executable, "-m", "pip"]
+            try:
+                subprocess.run(pip_cmd + ["--version"], cwd=PROJECT_ROOT, check=True, capture_output=True)
+            except subprocess.CalledProcessError:
+                subprocess.run(
+                    [sys.executable, "-m", "ensurepip", "--upgrade", "--default-pip"],
+                    cwd=PROJECT_ROOT,
+                    check=True,
+                )
            try:
                subprocess.run(pip_cmd + ["install", "-e", ".[all]", "--quiet"], cwd=PROJECT_ROOT, check=True)
            except subprocess.CalledProcessError:
@@ -2824,10 +2943,15 @@ def cmd_update(args):
                print(f"  ℹ️  {len(missing_config)} new config option(s) available")
            
            print()
-            if sys.stdin.isatty():
-                response = input("Would you like to configure them now? [Y/n]: ").strip().lower()
-            else:
+            if not (sys.stdin.isatty() and sys.stdout.isatty()):
+                print("  ℹ Non-interactive session — skipping config migration prompt.")
+                print("    Run 'hermes config migrate' later to apply any new config/env options.")
                response = "n"
+            else:
+                try:
+                    response = input("Would you like to configure them now? [Y/n]: ").strip().lower()
+                except EOFError:
+                    response = "n"
            
            if response in ('', 'y', 'yes'):
                print()
@@ -2875,10 +2999,11 @@ def cmd_update(args):
            # Check for macOS launchd service
            if is_macos():
                try:
+                    from hermes_cli.gateway import get_launchd_label
                    plist_path = get_launchd_plist_path()
                    if plist_path.exists():
                        check = subprocess.run(
-                            ["launchctl", "list", "ai.hermes.gateway"],
+                            ["launchctl", "list", get_launchd_label()],
                            capture_output=True, text=True, timeout=5,
                        )
                        has_launchd_service = check.returncode == 0
@@ -2934,12 +3059,13 @@ def cmd_update(args):
                    # after a manual SIGTERM, which would race with the
                    # PID file cleanup.
                    print("→ Restarting gateway service...")
+                    _launchd_label = get_launchd_label()
                    stop = subprocess.run(
-                        ["launchctl", "stop", "ai.hermes.gateway"],
+                        ["launchctl", "stop", _launchd_label],
                        capture_output=True, text=True, timeout=10,
                    )
                    start = subprocess.run(
-                        ["launchctl", "start", "ai.hermes.gateway"],
+                        ["launchctl", "start", _launchd_label],
                        capture_output=True, text=True, timeout=10,
                    )
                    if start.returncode == 0:
@@ -3122,7 +3248,7 @@ For more help on a command:
    )
    chat_parser.add_argument(
        "--provider",
-        choices=["auto", "openrouter", "nous", "openai-codex", "copilot-acp", "copilot", "anthropic", "zai", "kimi-coding", "minimax", "minimax-cn", "kilocode"],
+        choices=["auto", "openrouter", "nous", "openai-codex", "copilot-acp", "copilot", "anthropic", "huggingface", "zai", "kimi-coding", "minimax", "minimax-cn", "kilocode"],
        default=None,
        help="Inference provider (default: auto)"
    )
@@ -3423,7 +3549,38 @@ For more help on a command:
    cron_subparsers.add_parser("tick", help="Run due jobs once and exit")

    cron_parser.set_defaults(func=cmd_cron)
-    
+
+    # =========================================================================
+    # webhook command
+    # =========================================================================
+    webhook_parser = subparsers.add_parser(
+        "webhook",
+        help="Manage dynamic webhook subscriptions",
+        description="Create, list, and remove webhook subscriptions for event-driven agent activation",
+    )
+    webhook_subparsers = webhook_parser.add_subparsers(dest="webhook_action")
+
+    wh_sub = webhook_subparsers.add_parser("subscribe", aliases=["add"], help="Create a webhook subscription")
+    wh_sub.add_argument("name", help="Route name (used in URL: /webhooks/<name>)")
+    wh_sub.add_argument("--prompt", default="", help="Prompt template with {dot.notation} payload refs")
+    wh_sub.add_argument("--events", default="", help="Comma-separated event types to accept")
+    wh_sub.add_argument("--description", default="", help="What this subscription does")
+    wh_sub.add_argument("--skills", default="", help="Comma-separated skill names to load")
+    wh_sub.add_argument("--deliver", default="log", help="Delivery target: log, telegram, discord, slack, etc.")
+    wh_sub.add_argument("--deliver-chat-id", default="", help="Target chat ID for cross-platform delivery")
+    wh_sub.add_argument("--secret", default="", help="HMAC secret (auto-generated if omitted)")
+
+    webhook_subparsers.add_parser("list", aliases=["ls"], help="List all dynamic subscriptions")
+
+    wh_rm = webhook_subparsers.add_parser("remove", aliases=["rm"], help="Remove a subscription")
+    wh_rm.add_argument("name", help="Subscription name to remove")
+
+    wh_test = webhook_subparsers.add_parser("test", help="Send a test POST to a webhook route")
+    wh_test.add_argument("name", help="Subscription name to test")
+    wh_test.add_argument("--payload", default="", help="JSON payload to send (default: test payload)")
+
+    webhook_parser.set_defaults(func=cmd_webhook)
+
    # =========================================================================
    # doctor command
    # =========================================================================
@@ -3556,7 +3713,7 @@ For more help on a command:
    skills_snapshot = skills_subparsers.add_parser("snapshot", help="Export/import skill configurations")
    snapshot_subparsers = skills_snapshot.add_subparsers(dest="snapshot_action")
    snap_export = snapshot_subparsers.add_parser("export", help="Export installed skills to a file")
-    snap_export.add_argument("output", help="Output JSON file path")
+    snap_export.add_argument("output", help="Output JSON file path (use - for stdout)")
    snap_import = snapshot_subparsers.add_parser("import", help="Import and install skills from a file")
    snap_import.add_argument("input", help="Input JSON file path")
    snap_import.add_argument("--force", action="store_true", help="Force install despite caution verdict")
@@ -3833,7 +3990,7 @@ For more help on a command:
    sessions_list.add_argument("--limit", type=int, default=20, help="Max sessions to show")

    sessions_export = sessions_subparsers.add_parser("export", help="Export sessions to a JSONL file")
-    sessions_export.add_argument("output", help="Output JSONL file path")
+    sessions_export.add_argument("output", help="Output JSONL file path (use - for stdout)")
    sessions_export.add_argument("--source", help="Filter by source")
    sessions_export.add_argument("--session-id", help="Export a specific session")

@@ -3914,15 +4071,25 @@ For more help on a command:
                if not data:
                    print(f"Session '{args.session_id}' not found.")
                    return
-                with open(args.output, "w", encoding="utf-8") as f:
-                    f.write(_json.dumps(data, ensure_ascii=False) + "\n")
-                print(f"Exported 1 session to {args.output}")
+                line = _json.dumps(data, ensure_ascii=False) + "\n"
+                if args.output == "-":
+                    import sys
+                    sys.stdout.write(line)
+                else:
+                    with open(args.output, "w", encoding="utf-8") as f:
+                        f.write(line)
+                    print(f"Exported 1 session to {args.output}")
            else:
                sessions = db.export_all(source=args.source)
-                with open(args.output, "w", encoding="utf-8") as f:
+                if args.output == "-":
+                    import sys
                    for s in sessions:
-                        f.write(_json.dumps(s, ensure_ascii=False) + "\n")
-                print(f"Exported {len(sessions)} sessions to {args.output}")
+                        sys.stdout.write(_json.dumps(s, ensure_ascii=False) + "\n")
+                else:
+                    with open(args.output, "w", encoding="utf-8") as f:
+                        for s in sessions:
+                            f.write(_json.dumps(s, ensure_ascii=False) + "\n")
+                    print(f"Exported {len(sessions)} sessions to {args.output}")

        elif action == "delete":
            resolved_session_id = db.resolve_session_id(args.session_id)
@@ -208,14 +208,31 @@ _PROVIDER_MODELS: dict[str, list[str]] = {
        "google/gemini-3-pro-preview",
        "google/gemini-3-flash-preview",
    ],
+    # Alibaba DashScope Coding platform (coding-intl) — default endpoint.
+    # Supports Qwen models + third-party providers (GLM, Kimi, MiniMax).
+    # Users with classic DashScope keys should override DASHSCOPE_BASE_URL
+    # to https://dashscope-intl.aliyuncs.com/compatible-mode/v1 (OpenAI-compat)
+    # or https://dashscope-intl.aliyuncs.com/apps/anthropic (Anthropic-compat).
    "alibaba": [
        "qwen3.5-plus",
-        "qwen3-max",
        "qwen3-coder-plus",
        "qwen3-coder-next",
-        "qwen-plus-latest",
-        "qwen3.5-flash",
-        "qwen-vl-max",
+        # Third-party models available on coding-intl
+        "glm-5",
+        "glm-4.7",
+        "kimi-k2.5",
+        "MiniMax-M2.5",
+    ],
+    # Curated HF model list — only agentic models that map to OpenRouter defaults.
+    "huggingface": [
+        "Qwen/Qwen3.5-397B-A17B",
+        "Qwen/Qwen3.5-35B-A3B",
+        "deepseek-ai/DeepSeek-V3.2",
+        "moonshotai/Kimi-K2.5",
+        "MiniMaxAI/MiniMax-M2.5",
+        "zai-org/GLM-5",
+        "XiaomiMiMo/MiMo-V2-Flash",
+        "moonshotai/Kimi-K2-Thinking",
    ],
 }

@@ -236,6 +253,7 @@ _PROVIDER_LABELS = {
    "ai-gateway": "AI Gateway",
    "kilocode": "Kilo Code",
    "alibaba": "Alibaba Cloud (DashScope)",
+    "huggingface": "Hugging Face",
    "custom": "Custom endpoint",
 }

@@ -271,6 +289,9 @@ _PROVIDER_ALIASES = {
    "aliyun": "alibaba",
    "qwen": "alibaba",
    "alibaba-cloud": "alibaba",
+    "hf": "huggingface",
+    "hugging-face": "huggingface",
+    "huggingface-hub": "huggingface",
 }


@@ -304,7 +325,7 @@ def list_available_providers() -> list[dict[str, str]]:
    # Canonical providers in display order
    _PROVIDER_ORDER = [
        "openrouter", "nous", "openai-codex", "copilot", "copilot-acp",
-        "zai", "kimi-coding", "minimax", "minimax-cn", "kilocode", "anthropic", "alibaba",
+        "huggingface", "zai", "kimi-coding", "minimax", "minimax-cn", "kilocode", "anthropic", "alibaba",
        "opencode-zen", "opencode-go",
        "ai-gateway", "deepseek", "custom",
    ]
@@ -385,16 +385,23 @@ class PluginManager:
    # Hook invocation
    # -----------------------------------------------------------------------

-    def invoke_hook(self, hook_name: str, **kwargs: Any) -> None:
+    def invoke_hook(self, hook_name: str, **kwargs: Any) -> List[Any]:
        """Call all registered callbacks for *hook_name*.

        Each callback is wrapped in its own try/except so a misbehaving
        plugin cannot break the core agent loop.
+
+        Returns a list of non-``None`` return values from callbacks.
+        This allows hooks like ``pre_llm_call`` to contribute context
+        that the agent core can collect and inject.
        """
        callbacks = self._hooks.get(hook_name, [])
+        results: List[Any] = []
        for cb in callbacks:
            try:
-                cb(**kwargs)
+                ret = cb(**kwargs)
+                if ret is not None:
+                    results.append(ret)
            except Exception as exc:
                logger.warning(
                    "Hook '%s' callback %s raised: %s",
@@ -402,6 +409,7 @@ class PluginManager:
                    getattr(cb, "__name__", repr(cb)),
                    exc,
                )
+        return results

    # -----------------------------------------------------------------------
    # Introspection
@@ -446,9 +454,12 @@ def discover_plugins() -> None:
    get_plugin_manager().discover_and_load()


-def invoke_hook(hook_name: str, **kwargs: Any) -> None:
-    """Invoke a lifecycle hook on all loaded plugins."""
-    get_plugin_manager().invoke_hook(hook_name, **kwargs)
+def invoke_hook(hook_name: str, **kwargs: Any) -> List[Any]:
+    """Invoke a lifecycle hook on all loaded plugins.
+
+    Returns a list of non-``None`` return values from plugin callbacks.
+    """
+    return get_plugin_manager().invoke_hook(hook_name, **kwargs)


 def get_plugin_tool_names() -> Set[str]:
@@ -63,8 +63,11 @@ def _get_model_config() -> Dict[str, Any]:
    model_cfg = config.get("model")
    if isinstance(model_cfg, dict):
        cfg = dict(model_cfg)
-        default = cfg.get("default", "").strip()
-        base_url = cfg.get("base_url", "").strip()
+        # Accept "model" as alias for "default" (users intuitively write model.model)
+        if not cfg.get("default") and cfg.get("model"):
+            cfg["default"] = cfg["model"]
+        default = (cfg.get("default") or "").strip()
+        base_url = (cfg.get("base_url") or "").strip()
        is_local = "localhost" in base_url or "127.0.0.1" in base_url
        is_fallback = not default or default == "anthropic/claude-opus-4.6"
        if is_local and is_fallback and base_url:
@@ -203,7 +206,7 @@ def _resolve_named_custom_runtime(
        or _detect_api_mode_for_url(base_url)
        or "chat_completions",
        "base_url": base_url,
-        "api_key": api_key,
+        "api_key": api_key or "no-key-required",
        "source": f"custom_provider:{custom_provider.get('name', requested_provider)}",
    }

@@ -407,12 +410,6 @@ def resolve_runtime_provider(
            # (e.g. https://api.minimax.io/anthropic, https://dashscope.../anthropic)
            elif base_url.rstrip("/").endswith("/anthropic"):
                api_mode = "anthropic_messages"
-            # MiniMax providers always use Anthropic Messages API.
-            # Auto-correct stale /v1 URLs (from old .env or config) to /anthropic.
-            elif provider in ("minimax", "minimax-cn"):
-                api_mode = "anthropic_messages"
-                if base_url.rstrip("/").endswith("/v1"):
-                    base_url = base_url.rstrip("/")[:-3] + "/anthropic"
        return {
            "provider": provider,
            "api_mode": api_mode,
@@ -80,6 +80,11 @@ _DEFAULT_PROVIDER_MODELS = {
    "minimax-cn": ["MiniMax-M2.7", "MiniMax-M2.7-highspeed", "MiniMax-M2.5", "MiniMax-M2.5-highspeed", "MiniMax-M2.1"],
    "ai-gateway": ["anthropic/claude-opus-4.6", "anthropic/claude-sonnet-4.6", "openai/gpt-5", "google/gemini-3-flash"],
    "kilocode": ["anthropic/claude-opus-4.6", "anthropic/claude-sonnet-4.6", "openai/gpt-5.4", "google/gemini-3-pro-preview", "google/gemini-3-flash-preview"],
+    "huggingface": [
+        "Qwen/Qwen3.5-397B-A17B", "Qwen/Qwen3-235B-A22B-Thinking-2507",
+        "Qwen/Qwen3-Coder-480B-A35B-Instruct", "deepseek-ai/DeepSeek-R1-0528",
+        "deepseek-ai/DeepSeek-V3.2", "moonshotai/Kimi-K2.5",
+    ],
 }


@@ -580,11 +585,11 @@ def _print_setup_summary(config: dict, hermes_home):
    else:
        tool_status.append(("Mixture of Agents", False, "OPENROUTER_API_KEY"))

-    # Web tools (Parallel, Firecrawl, or Tavily)
-    if get_env_value("PARALLEL_API_KEY") or get_env_value("FIRECRAWL_API_KEY") or get_env_value("FIRECRAWL_API_URL") or get_env_value("TAVILY_API_KEY"):
+    # Web tools (Exa, Parallel, Firecrawl, or Tavily)
+    if get_env_value("EXA_API_KEY") or get_env_value("PARALLEL_API_KEY") or get_env_value("FIRECRAWL_API_KEY") or get_env_value("FIRECRAWL_API_URL") or get_env_value("TAVILY_API_KEY"):
        tool_status.append(("Web Search & Extract", True, None))
    else:
-        tool_status.append(("Web Search & Extract", False, "PARALLEL_API_KEY, FIRECRAWL_API_KEY, or TAVILY_API_KEY"))
+        tool_status.append(("Web Search & Extract", False, "EXA_API_KEY, PARALLEL_API_KEY, FIRECRAWL_API_KEY, or TAVILY_API_KEY"))

    # Browser tools (local Chromium or Browserbase cloud)
    import shutil
@@ -884,6 +889,7 @@ def setup_model_provider(config: dict):
        "OpenCode Go (open models, $10/month subscription)",
        "GitHub Copilot (uses GITHUB_TOKEN or gh auth token)",
        "GitHub Copilot ACP (spawns `copilot --acp --stdio`)",
+        "Hugging Face Inference Providers (20+ open models)",
    ]
    if keep_label:
        provider_choices.append(keep_label)
@@ -1528,7 +1534,26 @@ def setup_model_provider(config: dict):
        _set_model_provider(config, "copilot-acp", pconfig.inference_base_url)
        selected_base_url = pconfig.inference_base_url

-    # else: provider_idx == 16 (Keep current) — only shown when a provider already exists
+    elif provider_idx == 16:  # Hugging Face Inference Providers
+        selected_provider = "huggingface"
+        print()
+        print_header("Hugging Face API Token")
+        pconfig = PROVIDER_REGISTRY["huggingface"]
+        print_info(f"Provider: {pconfig.name}")
+        print_info("Get your token at: https://huggingface.co/settings/tokens")
+        print_info("Required permission: 'Make calls to Inference Providers'")
+        print()
+
+        api_key = prompt("  HF Token", password=True)
+        if api_key:
+            save_env_value("HF_TOKEN", api_key)
+            # Clear OpenRouter env vars to prevent routing confusion
+            save_env_value("OPENAI_BASE_URL", "")
+            save_env_value("OPENAI_API_KEY", "")
+        _set_model_provider(config, "huggingface", pconfig.inference_base_url)
+        selected_base_url = pconfig.inference_base_url
+
+    # else: provider_idx == 17 (Keep current) — only shown when a provider already exists
    # Normalize "keep current" to an explicit provider so downstream logic
    # doesn't fall back to the generic OpenRouter/static-model path.
    if selected_provider is None:
@@ -2067,11 +2092,11 @@ def setup_terminal_backend(config: dict):
        print_info("Serverless cloud sandboxes. Each session gets its own container.")
        print_info("Requires a Modal account: https://modal.com")

-        # Check if swe-rex[modal] is installed
+        # Check if modal SDK is installed
        try:
-            __import__("swe_rex")
+            __import__("modal")
        except ImportError:
-            print_info("Installing swe-rex[modal]...")
+            print_info("Installing modal SDK...")
            import subprocess

            uv_bin = shutil.which("uv")
@@ -2083,22 +2108,22 @@ def setup_terminal_backend(config: dict):
                        "install",
                        "--python",
                        sys.executable,
-                        "swe-rex[modal]",
+                        "modal",
                    ],
                    capture_output=True,
                    text=True,
                )
            else:
                result = subprocess.run(
-                    [sys.executable, "-m", "pip", "install", "swe-rex[modal]"],
+                    [sys.executable, "-m", "pip", "install", "modal"],
                    capture_output=True,
                    text=True,
                )
            if result.returncode == 0:
-                print_success("swe-rex[modal] installed")
+                print_success("modal SDK installed")
            else:
                print_warning(
-                    "Install failed — run manually: pip install 'swe-rex[modal]'"
+                    "Install failed — run manually: pip install modal"
                )

        # Modal token
@@ -2968,6 +2993,95 @@ def setup_tools(config: dict, first_install: bool = False):
    tools_command(first_install=first_install, config=config)


+# =============================================================================
+# Post-Migration Section Skip Logic
+# =============================================================================
+
+
+def _get_section_config_summary(config: dict, section_key: str) -> Optional[str]:
+    """Return a short summary if a setup section is already configured, else None.
+
+    Used after OpenClaw migration to detect which sections can be skipped.
+    ``get_env_value`` is the module-level import from hermes_cli.config
+    so that test patches on ``setup_mod.get_env_value`` take effect.
+    """
+    if section_key == "model":
+        has_key = bool(
+            get_env_value("OPENROUTER_API_KEY")
+            or get_env_value("OPENAI_API_KEY")
+            or get_env_value("ANTHROPIC_API_KEY")
+        )
+        if not has_key:
+            # Check for OAuth providers
+            try:
+                from hermes_cli.auth import get_active_provider
+                if get_active_provider():
+                    has_key = True
+            except Exception:
+                pass
+        if not has_key:
+            return None
+        model = config.get("model")
+        if isinstance(model, str) and model.strip():
+            return model.strip()
+        if isinstance(model, dict):
+            return str(model.get("default") or model.get("model") or "configured")
+        return "configured"
+
+    elif section_key == "terminal":
+        backend = config.get("terminal", {}).get("backend", "local")
+        return f"backend: {backend}"
+
+    elif section_key == "agent":
+        max_turns = config.get("agent", {}).get("max_turns", 90)
+        return f"max turns: {max_turns}"
+
+    elif section_key == "gateway":
+        platforms = []
+        if get_env_value("TELEGRAM_BOT_TOKEN"):
+            platforms.append("Telegram")
+        if get_env_value("DISCORD_BOT_TOKEN"):
+            platforms.append("Discord")
+        if get_env_value("SLACK_BOT_TOKEN"):
+            platforms.append("Slack")
+        if get_env_value("WHATSAPP_PHONE_NUMBER_ID"):
+            platforms.append("WhatsApp")
+        if get_env_value("SIGNAL_ACCOUNT"):
+            platforms.append("Signal")
+        if platforms:
+            return ", ".join(platforms)
+        return None  # No platforms configured — section must run
+
+    elif section_key == "tools":
+        tools = []
+        if get_env_value("ELEVENLABS_API_KEY"):
+            tools.append("TTS/ElevenLabs")
+        if get_env_value("BROWSERBASE_API_KEY"):
+            tools.append("Browser")
+        if get_env_value("FIRECRAWL_API_KEY"):
+            tools.append("Firecrawl")
+        if tools:
+            return ", ".join(tools)
+        return None
+
+    return None
+
+
+def _skip_configured_section(
+    config: dict, section_key: str, label: str
+) -> bool:
+    """Show an already-configured section summary and offer to skip.
+
+    Returns True if the user chose to skip, False if the section should run.
+    """
+    summary = _get_section_config_summary(config, section_key)
+    if not summary:
+        return False
+    print()
+    print_success(f"  {label}: {summary}")
+    return not prompt_yes_no(f"  Reconfigure {label.lower()}?", default=False)
+
+
 # =============================================================================
 # OpenClaw Migration
 # =============================================================================
@@ -3039,7 +3153,7 @@ def _offer_openclaw_migration(hermes_home: Path) -> bool:
            target_root=hermes_home.resolve(),
            execute=True,
            workspace_target=None,
-            overwrite=False,
+            overwrite=True,
            migrate_secrets=True,
            output_dir=None,
            selected_options=selected,
@@ -3195,6 +3309,8 @@ def run_setup_wizard(args):
        )
    )

+    migration_ran = False
+
    if is_existing:
        # ── Returning User Menu ──
        print()
@@ -3264,7 +3380,8 @@ def run_setup_wizard(args):
            return

        # Offer OpenClaw migration before configuration begins
-        if _offer_openclaw_migration(hermes_home):
+        migration_ran = _offer_openclaw_migration(hermes_home)
+        if migration_ran:
            # Reload config in case migration wrote to it
            config = load_config()

@@ -3277,20 +3394,31 @@ def run_setup_wizard(args):
    print()
    print_info("You can edit these files directly or use 'hermes config edit'")

+    if migration_ran:
+        print()
+        print_info("Settings were imported from OpenClaw.")
+        print_info("Each section below will show what was imported — press Enter to keep,")
+        print_info("or choose to reconfigure if needed.")
+
    # Section 1: Model & Provider
-    setup_model_provider(config)
+    if not (migration_ran and _skip_configured_section(config, "model", "Model & Provider")):
+        setup_model_provider(config)

    # Section 2: Terminal Backend
-    setup_terminal_backend(config)
+    if not (migration_ran and _skip_configured_section(config, "terminal", "Terminal Backend")):
+        setup_terminal_backend(config)

    # Section 3: Agent Settings
-    setup_agent_settings(config)
+    if not (migration_ran and _skip_configured_section(config, "agent", "Agent Settings")):
+        setup_agent_settings(config)

    # Section 4: Messaging Platforms
-    setup_gateway(config)
+    if not (migration_ran and _skip_configured_section(config, "gateway", "Messaging Platforms")):
+        setup_gateway(config)

    # Section 5: Tools
-    setup_tools(config, first_install=not is_existing)
+    if not (migration_ran and _skip_configured_section(config, "tools", "Tools")):
+        setup_tools(config, first_install=not is_existing)

    # Save and show summary
    save_config(config)
@@ -24,6 +24,10 @@ PLATFORMS = {
    "whatsapp": "📱 WhatsApp",
    "signal":   "📡 Signal",
    "email":    "📧 Email",
+    "homeassistant": "🏠 Home Assistant",
+    "mattermost": "💬 Mattermost",
+    "matrix":   "💬 Matrix",
+    "dingtalk": "💬 DingTalk",
 }

 # ─── Config Helpers ───────────────────────────────────────────────────────────
@@ -304,7 +304,8 @@ def do_browse(page: int = 1, page_size: int = 20, source: str = "all",


 def do_install(identifier: str, category: str = "", force: bool = False,
-               console: Optional[Console] = None, skip_confirm: bool = False) -> None:
+               console: Optional[Console] = None, skip_confirm: bool = False,
+               invalidate_cache: bool = True) -> None:
    """Fetch, quarantine, scan, confirm, and install a skill."""
    from tools.skills_hub import (
        GitHubAuth, create_source_router, ensure_hub_dirs,
@@ -417,6 +418,17 @@ def do_install(identifier: str, category: str = "", force: bool = False,
    c.print(f"[bold green]Installed:[/] {install_dir.relative_to(SKILLS_DIR)}")
    c.print(f"[dim]Files: {', '.join(bundle.files.keys())}[/]\n")

+    if invalidate_cache:
+        # Invalidate the skills prompt cache so the new skill appears immediately
+        try:
+            from agent.prompt_builder import clear_skills_system_prompt_cache
+            clear_skills_system_prompt_cache(clear_snapshot=True)
+        except Exception:
+            pass
+    else:
+        c.print("[dim]Skill will be available in your next session.[/]")
+        c.print("[dim]Use /reset to start a new session now, or --now to activate immediately (invalidates prompt cache).[/]\n")
+

 def do_inspect(identifier: str, console: Optional[Console] = None) -> None:
    """Preview a skill's SKILL.md content without installing."""
@@ -603,7 +615,8 @@ def do_audit(name: Optional[str] = None, console: Optional[Console] = None) -> N


 def do_uninstall(name: str, console: Optional[Console] = None,
-                 skip_confirm: bool = False) -> None:
+                 skip_confirm: bool = False,
+                 invalidate_cache: bool = True) -> None:
    """Remove a hub-installed skill with confirmation."""
    from tools.skills_hub import uninstall_skill

@@ -623,6 +636,15 @@ def do_uninstall(name: str, console: Optional[Console] = None,
    success, msg = uninstall_skill(name)
    if success:
        c.print(f"[bold green]{msg}[/]\n")
+        if invalidate_cache:
+            try:
+                from agent.prompt_builder import clear_skills_system_prompt_cache
+                clear_skills_system_prompt_cache(clear_snapshot=True)
+            except Exception:
+                pass
+        else:
+            c.print("[dim]Change will take effect in your next session.[/]")
+            c.print("[dim]Use /reset to start a new session now, or --now to apply immediately (invalidates prompt cache).[/]\n")
    else:
        c.print(f"[bold red]Error:[/] {msg}\n")

@@ -865,10 +887,15 @@ def do_snapshot_export(output_path: str, console: Optional[Console] = None) -> N
        "taps": tap_list,
    }

-    out = Path(output_path)
-    out.write_text(json.dumps(snapshot, indent=2, ensure_ascii=False) + "\n")
-    c.print(f"[bold green]Snapshot exported:[/] {out}")
-    c.print(f"[dim]{len(installed)} skill(s), {len(tap_list)} tap(s)[/]\n")
+    payload = json.dumps(snapshot, indent=2, ensure_ascii=False) + "\n"
+    if output_path == "-":
+        import sys
+        sys.stdout.write(payload)
+    else:
+        out = Path(output_path)
+        out.write_text(payload)
+        c.print(f"[bold green]Snapshot exported:[/] {out}")
+        c.print(f"[dim]{len(installed)} skill(s), {len(tap_list)} tap(s)[/]\n")


 def do_snapshot_import(input_path: str, force: bool = False,
@@ -1059,19 +1086,23 @@ def handle_skills_slash(cmd: str, console: Optional[Console] = None) -> None:

    elif action == "install":
        if not args:
-            c.print("[bold red]Usage:[/] /skills install <identifier> [--category <cat>] [--force|--yes]\n")
+            c.print("[bold red]Usage:[/] /skills install <identifier> [--category <cat>] [--force] [--now]\n")
            return
        identifier = args[0]
        category = ""
-        # --yes / -y bypasses confirmation prompt (needed in TUI mode)
-        # --force handles reinstall override
-        skip_confirm = any(flag in args for flag in ("--yes", "-y"))
+        # Slash commands run inside prompt_toolkit where input() hangs.
+        # Always skip confirmation — the user typing the command is implicit consent.
+        skip_confirm = True
        force = "--force" in args
+        # --now invalidates prompt cache immediately (costs more money).
+        # Default: defer to next session to preserve cache.
+        invalidate_cache = "--now" in args
        for i, a in enumerate(args):
            if a == "--category" and i + 1 < len(args):
                category = args[i + 1]
        do_install(identifier, category=category, force=force,
-                   skip_confirm=skip_confirm, console=c)
+                   skip_confirm=skip_confirm, invalidate_cache=invalidate_cache,
+                   console=c)

    elif action == "inspect":
        if not args:
@@ -1101,10 +1132,13 @@ def handle_skills_slash(cmd: str, console: Optional[Console] = None) -> None:

    elif action == "uninstall":
        if not args:
-            c.print("[bold red]Usage:[/] /skills uninstall <name> [--yes]\n")
+            c.print("[bold red]Usage:[/] /skills uninstall <name> [--now]\n")
            return
-        skip_confirm = any(flag in args for flag in ("--yes", "-y"))
-        do_uninstall(args[0], console=c, skip_confirm=skip_confirm)
+        # Slash commands run inside prompt_toolkit where input() hangs.
+        skip_confirm = True
+        invalidate_cache = "--now" in args
+        do_uninstall(args[0], console=c, skip_confirm=skip_confirm,
+                     invalidate_cache=invalidate_cache)

    elif action == "publish":
        if not args:
@@ -292,8 +292,9 @@ def show_status(args):
        print("  Manager:      systemd (user)")
        
    elif sys.platform == 'darwin':
+        from hermes_cli.gateway import get_launchd_label
        result = subprocess.run(
-            ["launchctl", "list", "ai.hermes.gateway"],
+            ["launchctl", "list", get_launchd_label()],
            capture_output=True,
            text=True
        )
@@ -108,7 +108,8 @@ def _get_effective_configurable_toolsets():
    """
    result = list(CONFIGURABLE_TOOLSETS)
    try:
-        from hermes_cli.plugins import get_plugin_toolsets
+        from hermes_cli.plugins import discover_plugins, get_plugin_toolsets
+        discover_plugins()  # idempotent — ensures plugins are loaded
        result.extend(get_plugin_toolsets())
    except Exception:
        pass
@@ -118,7 +119,8 @@ def _get_effective_configurable_toolsets():
 def _get_plugin_toolset_keys() -> set:
    """Return the set of toolset keys provided by plugins."""
    try:
-        from hermes_cli.plugins import get_plugin_toolsets
+        from hermes_cli.plugins import discover_plugins, get_plugin_toolsets
+        discover_plugins()  # idempotent — ensures plugins are loaded
        return {ts_key for ts_key, _, _ in get_plugin_toolsets()}
    except Exception:
        return set()
@@ -133,8 +135,10 @@ PLATFORMS = {
    "signal":   {"label": "📡 Signal",     "default_toolset": "hermes-signal"},
    "homeassistant": {"label": "🏠 Home Assistant", "default_toolset": "hermes-homeassistant"},
    "email":    {"label": "📧 Email",      "default_toolset": "hermes-email"},
+    "matrix":   {"label": "💬 Matrix",     "default_toolset": "hermes-matrix"},
    "dingtalk": {"label": "💬 DingTalk",   "default_toolset": "hermes-dingtalk"},
    "api_server": {"label": "🌐 API Server", "default_toolset": "hermes-api-server"},
+    "mattermost": {"label": "💬 Mattermost", "default_toolset": "hermes-mattermost"},
 }


@@ -186,6 +190,14 @@ TOOL_CATEGORIES = {
                    {"key": "FIRECRAWL_API_KEY", "prompt": "Firecrawl API key", "url": "https://firecrawl.dev"},
                ],
            },
+            {
+                "name": "Exa",
+                "tag": "AI-native search and contents",
+                "web_backend": "exa",
+                "env_vars": [
+                    {"key": "EXA_API_KEY", "prompt": "Exa API key", "url": "https://exa.ai"},
+                ],
+            },
            {
                "name": "Parallel",
                "tag": "AI-native search and extract",
@@ -0,0 +1,256 @@
+"""hermes webhook — manage dynamic webhook subscriptions from the CLI.
+
+Usage:
+    hermes webhook subscribe <name> [options]
+    hermes webhook list
+    hermes webhook remove <name>
+    hermes webhook test <name> [--payload '{"key": "value"}']
+
+Subscriptions persist to ~/.hermes/webhook_subscriptions.json and are
+hot-reloaded by the webhook adapter without a gateway restart.
+"""
+
+import json
+import os
+import re
+import secrets
+import time
+from pathlib import Path
+from typing import Dict, Optional
+
+
+_SUBSCRIPTIONS_FILENAME = "webhook_subscriptions.json"
+
+
+def _hermes_home() -> Path:
+    return Path(
+        os.getenv("HERMES_HOME", str(Path.home() / ".hermes"))
+    ).expanduser()
+
+
+def _subscriptions_path() -> Path:
+    return _hermes_home() / _SUBSCRIPTIONS_FILENAME
+
+
+def _load_subscriptions() -> Dict[str, dict]:
+    path = _subscriptions_path()
+    if not path.exists():
+        return {}
+    try:
+        data = json.loads(path.read_text(encoding="utf-8"))
+        return data if isinstance(data, dict) else {}
+    except Exception:
+        return {}
+
+
+def _save_subscriptions(subs: Dict[str, dict]) -> None:
+    path = _subscriptions_path()
+    path.parent.mkdir(parents=True, exist_ok=True)
+    tmp_path = path.with_suffix(".tmp")
+    tmp_path.write_text(
+        json.dumps(subs, indent=2, ensure_ascii=False),
+        encoding="utf-8",
+    )
+    os.replace(str(tmp_path), str(path))
+
+
+def _get_webhook_config() -> dict:
+    """Load webhook platform config. Returns {} if not configured."""
+    try:
+        from hermes_cli.config import load_config
+        cfg = load_config()
+        return cfg.get("platforms", {}).get("webhook", {})
+    except Exception:
+        return {}
+
+
+def _is_webhook_enabled() -> bool:
+    return bool(_get_webhook_config().get("enabled"))
+
+
+def _get_webhook_base_url() -> str:
+    wh = _get_webhook_config().get("extra", {})
+    host = wh.get("host", "0.0.0.0")
+    port = wh.get("port", 8644)
+    display_host = "localhost" if host == "0.0.0.0" else host
+    return f"http://{display_host}:{port}"
+
+
+_SETUP_HINT = """
+  Webhook platform is not enabled. To set it up:
+
+  1. Run the gateway setup wizard:
+     hermes gateway setup
+
+  2. Or manually add to ~/.hermes/config.yaml:
+     platforms:
+       webhook:
+         enabled: true
+         extra:
+           host: "0.0.0.0"
+           port: 8644
+           secret: "your-global-hmac-secret"
+
+  3. Or set environment variables in ~/.hermes/.env:
+     WEBHOOK_ENABLED=true
+     WEBHOOK_PORT=8644
+     WEBHOOK_SECRET=your-global-secret
+
+  Then start the gateway: hermes gateway run
+"""
+
+
+def _require_webhook_enabled() -> bool:
+    """Check webhook is enabled. Print setup guide and return False if not."""
+    if _is_webhook_enabled():
+        return True
+    print(_SETUP_HINT)
+    return False
+
+
+def webhook_command(args):
+    """Entry point for 'hermes webhook' subcommand."""
+    sub = getattr(args, "webhook_action", None)
+
+    if not sub:
+        print("Usage: hermes webhook {subscribe|list|remove|test}")
+        print("Run 'hermes webhook --help' for details.")
+        return
+
+    if not _require_webhook_enabled():
+        return
+
+    if sub in ("subscribe", "add"):
+        _cmd_subscribe(args)
+    elif sub in ("list", "ls"):
+        _cmd_list(args)
+    elif sub in ("remove", "rm"):
+        _cmd_remove(args)
+    elif sub == "test":
+        _cmd_test(args)
+
+
+def _cmd_subscribe(args):
+    name = args.name.strip().lower().replace(" ", "-")
+    if not re.match(r'^[a-z0-9][a-z0-9_-]*$', name):
+        print(f"Error: Invalid name '{name}'. Use lowercase alphanumeric with hyphens/underscores.")
+        return
+
+    subs = _load_subscriptions()
+    is_update = name in subs
+
+    secret = args.secret or secrets.token_urlsafe(32)
+    events = [e.strip() for e in args.events.split(",")] if args.events else []
+
+    route = {
+        "description": args.description or f"Agent-created subscription: {name}",
+        "events": events,
+        "secret": secret,
+        "prompt": args.prompt or "",
+        "skills": [s.strip() for s in args.skills.split(",")] if args.skills else [],
+        "deliver": args.deliver or "log",
+        "created_at": time.strftime("%Y-%m-%dT%H:%M:%SZ", time.gmtime()),
+    }
+
+    if args.deliver_chat_id:
+        route["deliver_extra"] = {"chat_id": args.deliver_chat_id}
+
+    subs[name] = route
+    _save_subscriptions(subs)
+
+    base_url = _get_webhook_base_url()
+    status = "Updated" if is_update else "Created"
+
+    print(f"\n  {status} webhook subscription: {name}")
+    print(f"  URL:    {base_url}/webhooks/{name}")
+    print(f"  Secret: {secret}")
+    if events:
+        print(f"  Events: {', '.join(events)}")
+    else:
+        print("  Events: (all)")
+    print(f"  Deliver: {route['deliver']}")
+    if route.get("prompt"):
+        prompt_preview = route["prompt"][:80] + ("..." if len(route["prompt"]) > 80 else "")
+        print(f"  Prompt: {prompt_preview}")
+    print(f"\n  Configure your service to POST to the URL above.")
+    print(f"  Use the secret for HMAC-SHA256 signature validation.")
+    print(f"  The gateway must be running to receive events (hermes gateway run).\n")
+
+
+def _cmd_list(args):
+    subs = _load_subscriptions()
+    if not subs:
+        print("  No dynamic webhook subscriptions.")
+        print("  Create one with: hermes webhook subscribe <name>")
+        return
+
+    base_url = _get_webhook_base_url()
+    print(f"\n  {len(subs)} webhook subscription(s):\n")
+    for name, route in subs.items():
+        events = ", ".join(route.get("events", [])) or "(all)"
+        deliver = route.get("deliver", "log")
+        desc = route.get("description", "")
+        print(f"  ◆ {name}")
+        if desc:
+            print(f"    {desc}")
+        print(f"    URL:     {base_url}/webhooks/{name}")
+        print(f"    Events:  {events}")
+        print(f"    Deliver: {deliver}")
+        print()
+
+
+def _cmd_remove(args):
+    name = args.name.strip().lower()
+    subs = _load_subscriptions()
+
+    if name not in subs:
+        print(f"  No subscription named '{name}'.")
+        print("  Note: Static routes from config.yaml cannot be removed here.")
+        return
+
+    del subs[name]
+    _save_subscriptions(subs)
+    print(f"  Removed webhook subscription: {name}")
+
+
+def _cmd_test(args):
+    """Send a test POST to a webhook route."""
+    name = args.name.strip().lower()
+    subs = _load_subscriptions()
+
+    if name not in subs:
+        print(f"  No subscription named '{name}'.")
+        return
+
+    route = subs[name]
+    secret = route.get("secret", "")
+    base_url = _get_webhook_base_url()
+    url = f"{base_url}/webhooks/{name}"
+
+    payload = args.payload or '{"test": true, "event_type": "test", "message": "Hello from hermes webhook test"}'
+
+    import hmac
+    import hashlib
+    sig = "sha256=" + hmac.new(
+        secret.encode(), payload.encode(), hashlib.sha256
+    ).hexdigest()
+
+    print(f"  Sending test POST to {url}")
+    try:
+        import urllib.request
+        req = urllib.request.Request(
+            url,
+            data=payload.encode(),
+            headers={
+                "Content-Type": "application/json",
+                "X-Hub-Signature-256": sig,
+                "X-GitHub-Event": "test",
+            },
+            method="POST",
+        )
+        with urllib.request.urlopen(req, timeout=10) as resp:
+            body = resp.read().decode()
+            print(f"  Response ({resp.status}): {body}")
+    except Exception as e:
+        print(f"  Error: {e}")
+        print("  Is the gateway running? (hermes gateway run)")
@@ -17,6 +17,27 @@ def get_hermes_home() -> Path:
    return Path(os.getenv("HERMES_HOME", Path.home() / ".hermes"))


+def get_hermes_dir(new_subpath: str, old_name: str) -> Path:
+    """Resolve a Hermes subdirectory with backward compatibility.
+
+    New installs get the consolidated layout (e.g. ``cache/images``).
+    Existing installs that already have the old path (e.g. ``image_cache``)
+    keep using it — no migration required.
+
+    Args:
+        new_subpath: Preferred path relative to HERMES_HOME (e.g. ``"cache/images"``).
+        old_name: Legacy path relative to HERMES_HOME (e.g. ``"image_cache"``).
+
+    Returns:
+        Absolute ``Path`` — old location if it exists on disk, otherwise the new one.
+    """
+    home = get_hermes_home()
+    old_path = home / old_name
+    if old_path.exists():
+        return old_path
+    return home / new_subpath
+
+
 VALID_REASONING_EFFORTS = ("xhigh", "high", "medium", "low", "minimal")


@@ -15,15 +15,20 @@ Key design decisions:
 """

 import json
+import logging
 import os
+import random
 import re
 import sqlite3
 import threading
 import time
 from pathlib import Path
 from hermes_constants import get_hermes_home
-from typing import Dict, Any, List, Optional
+from typing import Any, Callable, Dict, List, Optional, TypeVar

+logger = logging.getLogger(__name__)
+
+T = TypeVar("T")

 DEFAULT_DB_PATH = get_hermes_home() / "state.db"

@@ -116,18 +121,38 @@ class SessionDB:
    single writer via WAL mode). Each method opens its own cursor.
    """

+    # ── Write-contention tuning ──
+    # With multiple hermes processes (gateway + CLI sessions + worktree agents)
+    # all sharing one state.db, WAL write-lock contention causes visible TUI
+    # freezes.  SQLite's built-in busy handler uses a deterministic sleep
+    # schedule that causes convoy effects under high concurrency.
+    #
+    # Instead, we keep the SQLite timeout short (1s) and handle retries at the
+    # application level with random jitter, which naturally staggers competing
+    # writers and avoids the convoy.
+    _WRITE_MAX_RETRIES = 15
+    _WRITE_RETRY_MIN_S = 0.020   # 20ms
+    _WRITE_RETRY_MAX_S = 0.150   # 150ms
+    # Attempt a PASSIVE WAL checkpoint every N successful writes.
+    _CHECKPOINT_EVERY_N_WRITES = 50
+
    def __init__(self, db_path: Path = None):
        self.db_path = db_path or DEFAULT_DB_PATH
        self.db_path.parent.mkdir(parents=True, exist_ok=True)

        self._lock = threading.Lock()
+        self._write_count = 0
        self._conn = sqlite3.connect(
            str(self.db_path),
            check_same_thread=False,
-            # 30s gives the WAL writer (CLI or gateway) time to finish a batch
-            # flush before the concurrent reader/writer gives up.  10s was too
-            # short when the CLI is doing frequent memory flushes.
-            timeout=30.0,
+            # Short timeout — application-level retry with random jitter
+            # handles contention instead of sitting in SQLite's internal
+            # busy handler for up to 30s.
+            timeout=1.0,
+            # Autocommit mode: Python's default isolation_level="" auto-starts
+            # transactions on DML, which conflicts with our explicit
+            # BEGIN IMMEDIATE.  None = we manage transactions ourselves.
+            isolation_level=None,
        )
        self._conn.row_factory = sqlite3.Row
        self._conn.execute("PRAGMA journal_mode=WAL")
@@ -135,6 +160,96 @@ class SessionDB:

        self._init_schema()

+    # ── Core write helper ──
+
+    def _execute_write(self, fn: Callable[[sqlite3.Connection], T]) -> T:
+        """Execute a write transaction with BEGIN IMMEDIATE and jitter retry.
+
+        *fn* receives the connection and should perform INSERT/UPDATE/DELETE
+        statements.  The caller must NOT call ``commit()`` — that's handled
+        here after *fn* returns.
+
+        BEGIN IMMEDIATE acquires the WAL write lock at transaction start
+        (not at commit time), so lock contention surfaces immediately.
+        On ``database is locked``, we release the Python lock, sleep a
+        random 20-150ms, and retry — breaking the convoy pattern that
+        SQLite's built-in deterministic backoff creates.
+
+        Returns whatever *fn* returns.
+        """
+        last_err: Optional[Exception] = None
+        for attempt in range(self._WRITE_MAX_RETRIES):
+            try:
+                with self._lock:
+                    self._conn.execute("BEGIN IMMEDIATE")
+                    try:
+                        result = fn(self._conn)
+                        self._conn.commit()
+                    except BaseException:
+                        try:
+                            self._conn.rollback()
+                        except Exception:
+                            pass
+                        raise
+                # Success — periodic best-effort checkpoint.
+                self._write_count += 1
+                if self._write_count % self._CHECKPOINT_EVERY_N_WRITES == 0:
+                    self._try_wal_checkpoint()
+                return result
+            except sqlite3.OperationalError as exc:
+                err_msg = str(exc).lower()
+                if "locked" in err_msg or "busy" in err_msg:
+                    last_err = exc
+                    if attempt < self._WRITE_MAX_RETRIES - 1:
+                        jitter = random.uniform(
+                            self._WRITE_RETRY_MIN_S,
+                            self._WRITE_RETRY_MAX_S,
+                        )
+                        time.sleep(jitter)
+                        continue
+                # Non-lock error or retries exhausted — propagate.
+                raise
+        # Retries exhausted (shouldn't normally reach here).
+        raise last_err or sqlite3.OperationalError(
+            "database is locked after max retries"
+        )
+
+    def _try_wal_checkpoint(self) -> None:
+        """Best-effort PASSIVE WAL checkpoint.  Never blocks, never raises.
+
+        Flushes committed WAL frames back into the main DB file for any
+        frames that no other connection currently needs.  Keeps the WAL
+        from growing unbounded when many processes hold persistent
+        connections.
+        """
+        try:
+            with self._lock:
+                result = self._conn.execute(
+                    "PRAGMA wal_checkpoint(PASSIVE)"
+                ).fetchone()
+                if result and result[1] > 0:
+                    logger.debug(
+                        "WAL checkpoint: %d/%d pages checkpointed",
+                        result[2], result[1],
+                    )
+        except Exception:
+            pass  # Best effort — never fatal.
+
+    def close(self):
+        """Close the database connection.
+
+        Attempts a PASSIVE WAL checkpoint first so that exiting processes
+        help keep the WAL file from growing unbounded.
+        """
+        with self._lock:
+            if self._conn:
+                try:
+                    self._conn.execute("PRAGMA wal_checkpoint(PASSIVE)")
+                except Exception:
+                    pass
+                self._conn.close()
+                self._conn = None
+
    def _init_schema(self):
        """Create tables and FTS if they don't exist, run migrations."""
        cursor = self._conn.cursor()
@@ -256,8 +371,8 @@ class SessionDB:
        parent_session_id: str = None,
    ) -> str:
        """Create a new session record. Returns the session_id."""
-        with self._lock:
-            self._conn.execute(
+        def _do(conn):
+            conn.execute(
                """INSERT OR IGNORE INTO sessions (id, source, user_id, model, model_config,
                   system_prompt, parent_session_id, started_at)
                   VALUES (?, ?, ?, ?, ?, ?, ?, ?)""",
@@ -272,26 +387,35 @@ class SessionDB:
                    time.time(),
                ),
            )
-            self._conn.commit()
+        self._execute_write(_do)
        return session_id

    def end_session(self, session_id: str, end_reason: str) -> None:
        """Mark a session as ended."""
-        with self._lock:
-            self._conn.execute(
+        def _do(conn):
+            conn.execute(
                "UPDATE sessions SET ended_at = ?, end_reason = ? WHERE id = ?",
                (time.time(), end_reason, session_id),
            )
-            self._conn.commit()
+        self._execute_write(_do)
+
+    def reopen_session(self, session_id: str) -> None:
+        """Clear ended_at/end_reason so a session can be resumed."""
+        def _do(conn):
+            conn.execute(
+                "UPDATE sessions SET ended_at = NULL, end_reason = NULL WHERE id = ?",
+                (session_id,),
+            )
+        self._execute_write(_do)

    def update_system_prompt(self, session_id: str, system_prompt: str) -> None:
        """Store the full assembled system prompt snapshot."""
-        with self._lock:
-            self._conn.execute(
+        def _do(conn):
+            conn.execute(
                "UPDATE sessions SET system_prompt = ? WHERE id = ?",
                (system_prompt, session_id),
            )
-            self._conn.commit()
+        self._execute_write(_do)

    def update_token_counts(
        self,
@@ -310,11 +434,39 @@ class SessionDB:
        billing_provider: Optional[str] = None,
        billing_base_url: Optional[str] = None,
        billing_mode: Optional[str] = None,
+        absolute: bool = False,
    ) -> None:
-        """Increment token counters and backfill model if not already set."""
-        with self._lock:
-            self._conn.execute(
-                """UPDATE sessions SET
+        """Update token counters and backfill model if not already set.
+
+        When *absolute* is False (default), values are **incremented** — use
+        this for per-API-call deltas (CLI path).
+
+        When *absolute* is True, values are **set directly** — use this when
+        the caller already holds cumulative totals (gateway path, where the
+        cached agent accumulates across messages).
+        """
+        if absolute:
+            sql = """UPDATE sessions SET
+                   input_tokens = ?,
+                   output_tokens = ?,
+                   cache_read_tokens = ?,
+                   cache_write_tokens = ?,
+                   reasoning_tokens = ?,
+                   estimated_cost_usd = COALESCE(?, 0),
+                   actual_cost_usd = CASE
+                       WHEN ? IS NULL THEN actual_cost_usd
+                       ELSE ?
+                   END,
+                   cost_status = COALESCE(?, cost_status),
+                   cost_source = COALESCE(?, cost_source),
+                   pricing_version = COALESCE(?, pricing_version),
+                   billing_provider = COALESCE(billing_provider, ?),
+                   billing_base_url = COALESCE(billing_base_url, ?),
+                   billing_mode = COALESCE(billing_mode, ?),
+                   model = COALESCE(model, ?)
+                   WHERE id = ?"""
+        else:
+            sql = """UPDATE sessions SET
                   input_tokens = input_tokens + ?,
                   output_tokens = output_tokens + ?,
                   cache_read_tokens = cache_read_tokens + ?,
@@ -332,6 +484,94 @@ class SessionDB:
                   billing_base_url = COALESCE(billing_base_url, ?),
                   billing_mode = COALESCE(billing_mode, ?),
                   model = COALESCE(model, ?)
+                   WHERE id = ?"""
+        params = (
+            input_tokens,
+            output_tokens,
+            cache_read_tokens,
+            cache_write_tokens,
+            reasoning_tokens,
+            estimated_cost_usd,
+            actual_cost_usd,
+            actual_cost_usd,
+            cost_status,
+            cost_source,
+            pricing_version,
+            billing_provider,
+            billing_base_url,
+            billing_mode,
+            model,
+            session_id,
+        )
+        def _do(conn):
+            conn.execute(sql, params)
+        self._execute_write(_do)
+
+    def ensure_session(
+        self,
+        session_id: str,
+        source: str = "unknown",
+        model: str = None,
+    ) -> None:
+        """Ensure a session row exists, creating it with minimal metadata if absent.
+
+        Used by _flush_messages_to_session_db to recover from a failed
+        create_session() call (e.g. transient SQLite lock at agent startup).
+        INSERT OR IGNORE is safe to call even when the row already exists.
+        """
+        def _do(conn):
+            conn.execute(
+                """INSERT OR IGNORE INTO sessions
+                   (id, source, model, started_at)
+                   VALUES (?, ?, ?, ?)""",
+                (session_id, source, model, time.time()),
+            )
+        self._execute_write(_do)
+
+    def set_token_counts(
+        self,
+        session_id: str,
+        input_tokens: int = 0,
+        output_tokens: int = 0,
+        model: str = None,
+        cache_read_tokens: int = 0,
+        cache_write_tokens: int = 0,
+        reasoning_tokens: int = 0,
+        estimated_cost_usd: Optional[float] = None,
+        actual_cost_usd: Optional[float] = None,
+        cost_status: Optional[str] = None,
+        cost_source: Optional[str] = None,
+        pricing_version: Optional[str] = None,
+        billing_provider: Optional[str] = None,
+        billing_base_url: Optional[str] = None,
+        billing_mode: Optional[str] = None,
+    ) -> None:
+        """Set token counters to absolute values (not increment).
+
+        Use this when the caller provides cumulative totals from a completed
+        conversation run (e.g. the gateway, where the cached agent's
+        session_prompt_tokens already reflects the running total).
+        """
+        def _do(conn):
+            conn.execute(
+                """UPDATE sessions SET
+                   input_tokens = ?,
+                   output_tokens = ?,
+                   cache_read_tokens = ?,
+                   cache_write_tokens = ?,
+                   reasoning_tokens = ?,
+                   estimated_cost_usd = ?,
+                   actual_cost_usd = CASE
+                       WHEN ? IS NULL THEN actual_cost_usd
+                       ELSE ?
+                   END,
+                   cost_status = COALESCE(?, cost_status),
+                   cost_source = COALESCE(?, cost_source),
+                   pricing_version = COALESCE(?, pricing_version),
+                   billing_provider = COALESCE(billing_provider, ?),
+                   billing_base_url = COALESCE(billing_base_url, ?),
+                   billing_mode = COALESCE(billing_mode, ?),
+                   model = COALESCE(model, ?)
                   WHERE id = ?""",
                (
                    input_tokens,
@@ -352,28 +592,7 @@ class SessionDB:
                    session_id,
                ),
            )
-            self._conn.commit()
-
-    def ensure_session(
-        self,
-        session_id: str,
-        source: str = "unknown",
-        model: str = None,
-    ) -> None:
-        """Ensure a session row exists, creating it with minimal metadata if absent.
-
-        Used by _flush_messages_to_session_db to recover from a failed
-        create_session() call (e.g. transient SQLite lock at agent startup).
-        INSERT OR IGNORE is safe to call even when the row already exists.
-        """
-        with self._lock:
-            self._conn.execute(
-                """INSERT OR IGNORE INTO sessions
-                   (id, source, model, started_at)
-                   VALUES (?, ?, ?, ?)""",
-                (session_id, source, model, time.time()),
-            )
-            self._conn.commit()
+        self._execute_write(_do)

    def get_session(self, session_id: str) -> Optional[Dict[str, Any]]:
        """Get a session by ID."""
@@ -467,10 +686,10 @@ class SessionDB:
        Empty/whitespace-only strings are normalized to None (clearing the title).
        """
        title = self.sanitize_title(title)
-        with self._lock:
+        def _do(conn):
            if title:
                # Check uniqueness (allow the same session to keep its own title)
-                cursor = self._conn.execute(
+                cursor = conn.execute(
                    "SELECT id FROM sessions WHERE title = ? AND id != ?",
                    (title, session_id),
                )
@@ -479,12 +698,12 @@ class SessionDB:
                    raise ValueError(
                        f"Title '{title}' is already in use by session {conflict['id']}"
                    )
-            cursor = self._conn.execute(
+            cursor = conn.execute(
                "UPDATE sessions SET title = ? WHERE id = ?",
                (title, session_id),
            )
-            self._conn.commit()
-            rowcount = cursor.rowcount
+            return cursor.rowcount
+        rowcount = self._execute_write(_do)
        return rowcount > 0

    def get_session_title(self, session_id: str) -> Optional[str]:
@@ -656,17 +875,24 @@ class SessionDB:
        Also increments the session's message_count (and tool_call_count
        if role is 'tool' or tool_calls is present).
        """
-        with self._lock:
-            # Serialize structured fields to JSON for storage
-            reasoning_details_json = (
-                json.dumps(reasoning_details)
-                if reasoning_details else None
-            )
-            codex_items_json = (
-                json.dumps(codex_reasoning_items)
-                if codex_reasoning_items else None
-            )
-            cursor = self._conn.execute(
+        # Serialize structured fields to JSON before entering the write txn
+        reasoning_details_json = (
+            json.dumps(reasoning_details)
+            if reasoning_details else None
+        )
+        codex_items_json = (
+            json.dumps(codex_reasoning_items)
+            if codex_reasoning_items else None
+        )
+        tool_calls_json = json.dumps(tool_calls) if tool_calls else None
+
+        # Pre-compute tool call count
+        num_tool_calls = 0
+        if tool_calls is not None:
+            num_tool_calls = len(tool_calls) if isinstance(tool_calls, list) else 1
+
+        def _do(conn):
+            cursor = conn.execute(
                """INSERT INTO messages (session_id, role, content, tool_call_id,
                   tool_calls, tool_name, timestamp, token_count, finish_reason,
                   reasoning, reasoning_details, codex_reasoning_items)
@@ -676,7 +902,7 @@ class SessionDB:
                    role,
                    content,
                    tool_call_id,
-                    json.dumps(tool_calls) if tool_calls else None,
+                    tool_calls_json,
                    tool_name,
                    time.time(),
                    token_count,
@@ -689,25 +915,20 @@ class SessionDB:
            msg_id = cursor.lastrowid

            # Update counters
-            # Count actual tool calls from the tool_calls list (not from tool responses).
-            # A single assistant message can contain multiple parallel tool calls.
-            num_tool_calls = 0
-            if tool_calls is not None:
-                num_tool_calls = len(tool_calls) if isinstance(tool_calls, list) else 1
            if num_tool_calls > 0:
-                self._conn.execute(
+                conn.execute(
                    """UPDATE sessions SET message_count = message_count + 1,
                       tool_call_count = tool_call_count + ? WHERE id = ?""",
                    (num_tool_calls, session_id),
                )
            else:
-                self._conn.execute(
+                conn.execute(
                    "UPDATE sessions SET message_count = message_count + 1 WHERE id = ?",
                    (session_id,),
                )
+            return msg_id

-            self._conn.commit()
-        return msg_id
+        return self._execute_write(_do)

    def get_messages(self, session_id: str) -> List[Dict[str, Any]]:
        """Load all messages for a session, ordered by timestamp."""
@@ -1001,54 +1222,53 @@ class SessionDB:

    def clear_messages(self, session_id: str) -> None:
        """Delete all messages for a session and reset its counters."""
-        with self._lock:
-            self._conn.execute(
+        def _do(conn):
+            conn.execute(
                "DELETE FROM messages WHERE session_id = ?", (session_id,)
            )
-            self._conn.execute(
+            conn.execute(
                "UPDATE sessions SET message_count = 0, tool_call_count = 0 WHERE id = ?",
                (session_id,),
            )
-            self._conn.commit()
+        self._execute_write(_do)

    def delete_session(self, session_id: str) -> bool:
        """Delete a session and all its messages. Returns True if found."""
-        with self._lock:
-            cursor = self._conn.execute(
+        def _do(conn):
+            cursor = conn.execute(
                "SELECT COUNT(*) FROM sessions WHERE id = ?", (session_id,)
            )
            if cursor.fetchone()[0] == 0:
                return False
-            self._conn.execute("DELETE FROM messages WHERE session_id = ?", (session_id,))
-            self._conn.execute("DELETE FROM sessions WHERE id = ?", (session_id,))
-            self._conn.commit()
+            conn.execute("DELETE FROM messages WHERE session_id = ?", (session_id,))
+            conn.execute("DELETE FROM sessions WHERE id = ?", (session_id,))
            return True
+        return self._execute_write(_do)

    def prune_sessions(self, older_than_days: int = 90, source: str = None) -> int:
        """
        Delete sessions older than N days. Returns count of deleted sessions.
        Only prunes ended sessions (not active ones).
        """
-        import time as _time
-        cutoff = _time.time() - (older_than_days * 86400)
+        cutoff = time.time() - (older_than_days * 86400)

-        with self._lock:
+        def _do(conn):
            if source:
-                cursor = self._conn.execute(
+                cursor = conn.execute(
                    """SELECT id FROM sessions
                       WHERE started_at < ? AND ended_at IS NOT NULL AND source = ?""",
                    (cutoff, source),
                )
            else:
-                cursor = self._conn.execute(
+                cursor = conn.execute(
                    "SELECT id FROM sessions WHERE started_at < ? AND ended_at IS NOT NULL",
                    (cutoff,),
                )
            session_ids = [row["id"] for row in cursor.fetchall()]

            for sid in session_ids:
-                self._conn.execute("DELETE FROM messages WHERE session_id = ?", (sid,))
-                self._conn.execute("DELETE FROM sessions WHERE id = ?", (sid,))
+                conn.execute("DELETE FROM messages WHERE session_id = ?", (sid,))
+                conn.execute("DELETE FROM sessions WHERE id = ?", (sid,))
+            return len(session_ids)

-            self._conn.commit()
-        return len(session_ids)
+        return self._execute_write(_do)
@@ -270,7 +270,7 @@ def cmd_status(args) -> None:
            print(f"    {peer}: {mode}")
    print(f"  Write freq:     {hcfg.write_frequency}")

-    if hcfg.enabled and hcfg.api_key:
+    if hcfg.enabled and (hcfg.api_key or hcfg.base_url):
        print("\n  Connection... ", end="", flush=True)
        try:
            get_honcho_client(hcfg)
@@ -278,7 +278,7 @@ def cmd_status(args) -> None:
        except Exception as e:
            print(f"FAILED ({e})\n")
    else:
-        reason = "disabled" if not hcfg.enabled else "no API key"
+        reason = "disabled" if not hcfg.enabled else "no API key or base URL"
        print(f"\n  Not connected ({reason})\n")


@@ -417,9 +417,18 @@ def get_honcho_client(config: HonchoClientConfig | None = None) -> Honcho:
    else:
        logger.info("Initializing Honcho client (host: %s, workspace: %s)", config.host, config.workspace_id)

+    # Local Honcho instances don't require an API key, but the SDK
+    # expects a non-empty string.  Use a placeholder for local URLs.
+    _is_local = resolved_base_url and (
+        "localhost" in resolved_base_url
+        or "127.0.0.1" in resolved_base_url
+        or "::1" in resolved_base_url
+    )
+    effective_api_key = config.api_key or ("local" if _is_local else None)
+
    kwargs: dict = {
        "workspace_id": config.workspace_id,
-        "api_key": config.api_key,
+        "api_key": effective_api_key,
        "environment": config.environment,
    }
    if resolved_base_url:
@@ -10,6 +10,12 @@
 # container recreation. Environment variables are written to $HERMES_HOME/.env
 # and read by hermes at startup — no container recreation needed for env changes.
 #
+# Tool resolution: the hermes wrapper uses --suffix PATH for nix store tools,
+# so apt/uv-installed versions take priority. The container entrypoint provisions
+# extensible tools on first boot: nodejs/npm via apt, uv via curl, and a Python
+# 3.11 venv (bootstrapped entirely by uv) at ~/.venv with pip seeded. Agents get
+# writable tool prefixes for npm i -g, pip install, uv tool install, etc.
+#
 # Usage:
 #   services.hermes-agent = {
 #     enable = true;
@@ -105,22 +111,52 @@
      fi
      mkdir -p "$TARGET_HOME"
      chown "$HERMES_UID:$HERMES_GID" "$TARGET_HOME"
+      chmod 0750 "$TARGET_HOME"

      # Ensure HERMES_HOME is owned by the target user
      if [ -n "''${HERMES_HOME:-}" ] && [ -d "$HERMES_HOME" ]; then
        chown -R "$HERMES_UID:$HERMES_GID" "$HERMES_HOME"
      fi

-      # Install sudo on Debian/Ubuntu if missing (first boot only, cached in writable layer)
-      if command -v apt-get >/dev/null 2>&1 && ! command -v sudo >/dev/null 2>&1; then
-        apt-get update -qq >/dev/null 2>&1 && apt-get install -y -qq sudo >/dev/null 2>&1 || true
+      # ── Provision apt packages (first boot only, cached in writable layer) ──
+      # sudo: agent self-modification
+      # nodejs/npm: writable node so npm i -g works (nix store copies are read-only)
+      # curl: needed for uv installer
+      if [ ! -f /var/lib/hermes-tools-provisioned ] && command -v apt-get >/dev/null 2>&1; then
+        echo "First boot: provisioning agent tools..."
+        apt-get update -qq
+        apt-get install -y -qq sudo nodejs npm curl
+        touch /var/lib/hermes-tools-provisioned
      fi
+
      if command -v sudo >/dev/null 2>&1 && [ ! -f /etc/sudoers.d/hermes ]; then
        mkdir -p /etc/sudoers.d
        echo "$TARGET_USER ALL=(ALL) NOPASSWD:ALL" > /etc/sudoers.d/hermes
        chmod 0440 /etc/sudoers.d/hermes
      fi

+      # uv (Python manager) — not in Ubuntu repos, retry-safe outside the sentinel
+      if ! command -v uv >/dev/null 2>&1 && [ ! -x "$TARGET_HOME/.local/bin/uv" ] && command -v curl >/dev/null 2>&1; then
+        su -s /bin/sh "$TARGET_USER" -c 'curl -LsSf https://astral.sh/uv/install.sh | sh' || true
+      fi
+
+      # Python 3.11 venv — gives the agent a writable Python with pip.
+      # Uses uv to install Python 3.11 (Ubuntu 24.04 ships 3.12).
+      # --seed includes pip/setuptools so bare `pip install` works.
+      _UV_BIN="$TARGET_HOME/.local/bin/uv"
+      if [ ! -d "$TARGET_HOME/.venv" ] && [ -x "$_UV_BIN" ]; then
+        su -s /bin/sh "$TARGET_USER" -c "
+          export PATH=\"\$HOME/.local/bin:\$PATH\"
+          uv python install 3.11
+          uv venv --python 3.11 --seed \"\$HOME/.venv\"
+        " || true
+      fi
+
+      # Put the agent venv first on PATH so python/pip resolve to writable copies
+      if [ -d "$TARGET_HOME/.venv/bin" ]; then
+        export PATH="$TARGET_HOME/.venv/bin:$PATH"
+      fi
+
      if command -v setpriv >/dev/null 2>&1; then
        exec setpriv --reuid="$HERMES_UID" --regid="$HERMES_GID" --init-groups "$@"
      elif command -v su >/dev/null 2>&1; then
@@ -516,8 +552,8 @@
      # ── Directories ───────────────────────────────────────────────────
      {
        systemd.tmpfiles.rules = [
-          "d ${cfg.stateDir}                0755 ${cfg.user} ${cfg.group} - -"
-          "d ${cfg.stateDir}/.hermes        0755 ${cfg.user} ${cfg.group} - -"
+          "d ${cfg.stateDir}                0750 ${cfg.user} ${cfg.group} - -"
+          "d ${cfg.stateDir}/.hermes        0750 ${cfg.user} ${cfg.group} - -"
          "d ${cfg.stateDir}/home           0750 ${cfg.user} ${cfg.group} - -"
          "d ${cfg.workingDirectory}         0750 ${cfg.user} ${cfg.group} - -"
        ];
@@ -531,21 +567,23 @@
          mkdir -p ${cfg.stateDir}/home
          mkdir -p ${cfg.workingDirectory}
          chown ${cfg.user}:${cfg.group} ${cfg.stateDir} ${cfg.stateDir}/.hermes ${cfg.stateDir}/home ${cfg.workingDirectory}
+          chmod 0750 ${cfg.stateDir} ${cfg.stateDir}/.hermes ${cfg.stateDir}/home ${cfg.workingDirectory}

          # Merge Nix settings into existing config.yaml.
          # Preserves user-added keys (skills, streaming, etc.); Nix keys win.
          # If configFile is user-provided (not generated), overwrite instead of merge.
          ${if cfg.configFile != null then ''
-            install -o ${cfg.user} -g ${cfg.group} -m 0644 -D ${configFile} ${cfg.stateDir}/.hermes/config.yaml
+            install -o ${cfg.user} -g ${cfg.group} -m 0640 -D ${configFile} ${cfg.stateDir}/.hermes/config.yaml
          '' else ''
            ${configMergeScript} ${generatedConfigFile} ${cfg.stateDir}/.hermes/config.yaml
            chown ${cfg.user}:${cfg.group} ${cfg.stateDir}/.hermes/config.yaml
-            chmod 0644 ${cfg.stateDir}/.hermes/config.yaml
+            chmod 0640 ${cfg.stateDir}/.hermes/config.yaml
          ''}

          # Managed mode marker (so interactive shells also detect NixOS management)
          touch ${cfg.stateDir}/.hermes/.managed
          chown ${cfg.user}:${cfg.group} ${cfg.stateDir}/.hermes/.managed
+          chmod 0644 ${cfg.stateDir}/.hermes/.managed

          # Seed auth file if provided
          ${lib.optionalString (cfg.authFile != null) ''
@@ -577,7 +615,7 @@ HERMES_NIX_ENV_EOF

          # Link documents into workspace
          ${lib.concatStringsSep "\n" (lib.mapAttrsToList (name: _value: ''
-            install -o ${cfg.user} -g ${cfg.group} -m 0644 ${documentDerivation}/${name} ${cfg.workingDirectory}/${name}
+            install -o ${cfg.user} -g ${cfg.group} -m 0640 ${documentDerivation}/${name} ${cfg.workingDirectory}/${name}
          '') cfg.documents)}
        '';
      }
@@ -35,7 +35,7 @@

          ${pkgs.lib.concatMapStringsSep "\n" (name: ''
            makeWrapper ${hermesVenv}/bin/${name} $out/bin/${name} \
-              --prefix PATH : "${runtimePath}" \
+              --suffix PATH : "${runtimePath}" \
              --set HERMES_BUNDLED_SKILLS $out/share/hermes-agent/skills
          '') [ "hermes" "hermes-agent" "hermes-acp" ]}

@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"

 [project]
 name = "hermes-agent"
-version = "0.4.0"
+version = "0.5.0"
 description = "The self-improving AI agent — creates skills from experience, improves them during use, and runs anywhere"
 readme = "README.md"
 requires-python = ">=3.11"
@@ -26,6 +26,7 @@ dependencies = [
  # Interactive CLI (prompt_toolkit is used directly by cli.py)
  "prompt_toolkit>=3.0.52,<4",
  # Tools
+  "exa-py>=2.9.0,<3",
  "firecrawl-py>=4.16.0,<5",
  "parallel-web>=0.4.2,<1",
  "fal-client>=0.13.1,<1",
@@ -37,7 +38,7 @@ dependencies = [
 ]

 [project.optional-dependencies]
-modal = ["swe-rex[modal]>=1.4.0,<2"]
+modal = ["modal>=1.0.0,<2"]
 daytona = ["daytona>=0.148.0,<1"]
 dev = ["pytest>=9.0.2,<10", "pytest-asyncio>=1.3.0,<2", "pytest-xdist>=3.0,<4", "mcp>=1.2.0,<2"]
 messaging = ["python-telegram-bot>=22.6,<23", "discord.py[voice]>=2.7.1,<3", "aiohttp>=3.13.3,<4", "slack-bolt>=1.18.0,<2", "slack-sdk>=3.27.0,<4"]
@@ -55,7 +56,7 @@ honcho = ["honcho-ai>=2.0.1,<3"]
 mcp = ["mcp>=1.2.0,<2"]
 homeassistant = ["aiohttp>=3.9.0,<4"]
 sms = ["aiohttp>=3.9.0,<4"]
-acp = ["agent-client-protocol>=0.8.1,<1.0"]
+acp = ["agent-client-protocol>=0.8.1,<0.9"]
 dingtalk = ["dingtalk-stream>=0.1.0,<1"]
 rl = [
  "atroposlib @ git+https://github.com/NousResearch/atropos.git",
@@ -62,7 +62,12 @@ else:


 # Import our tool system
-from model_tools import get_tool_definitions, handle_function_call, check_toolset_requirements
+from model_tools import (
+    get_tool_definitions,
+    get_toolset_for_tool,
+    handle_function_call,
+    check_toolset_requirements,
+)
 from tools.terminal_tool import cleanup_vm
 from tools.interrupt import set_interrupt as _set_interrupt
 from tools.browser_tool import cleanup_browser
@@ -83,7 +88,7 @@ from agent.model_metadata import (
 )
 from agent.context_compressor import ContextCompressor
 from agent.prompt_caching import apply_anthropic_cache_control
-from agent.prompt_builder import build_skills_system_prompt, build_context_files_prompt, load_soul_md
+from agent.prompt_builder import build_skills_system_prompt, build_context_files_prompt, load_soul_md, TOOL_USE_ENFORCEMENT_GUIDANCE, TOOL_USE_ENFORCEMENT_MODELS
 from agent.usage_pricing import estimate_usage_cost, normalize_usage
 from agent.display import (
    KawaiiSpinner, build_tool_preview as _build_tool_preview,
@@ -356,6 +361,85 @@ def _inject_honcho_turn_context(content, turn_context: str):
    return f"{text}\n\n{note}"


+# Budget warning text patterns injected by _get_budget_warning().
+_BUDGET_WARNING_RE = re.compile(
+    r"\[BUDGET(?:\s+WARNING)?:\s+Iteration\s+\d+/\d+\..*?\]",
+    re.DOTALL,
+)
+
+
+# Regex to match lone surrogate code points (U+D800..U+DFFF).
+# These are invalid in UTF-8 and cause UnicodeEncodeError when the OpenAI SDK
+# serialises messages to JSON.  Common source: clipboard paste from Google Docs
+# or other rich-text editors on some platforms.
+_SURROGATE_RE = re.compile(r'[\ud800-\udfff]')
+
+
+def _sanitize_surrogates(text: str) -> str:
+    """Replace lone surrogate code points with U+FFFD (replacement character).
+
+    Surrogates are invalid in UTF-8 and will crash ``json.dumps()`` inside the
+    OpenAI SDK.  This is a fast no-op when the text contains no surrogates.
+    """
+    if _SURROGATE_RE.search(text):
+        return _SURROGATE_RE.sub('\ufffd', text)
+    return text
+
+
+def _sanitize_messages_surrogates(messages: list) -> bool:
+    """Sanitize surrogate characters from all string content in a messages list.
+
+    Walks message dicts in-place.  Returns True if any surrogates were found
+    and replaced, False otherwise.
+    """
+    found = False
+    for msg in messages:
+        if not isinstance(msg, dict):
+            continue
+        content = msg.get("content")
+        if isinstance(content, str) and _SURROGATE_RE.search(content):
+            msg["content"] = _SURROGATE_RE.sub('\ufffd', content)
+            found = True
+        elif isinstance(content, list):
+            for part in content:
+                if isinstance(part, dict):
+                    text = part.get("text")
+                    if isinstance(text, str) and _SURROGATE_RE.search(text):
+                        part["text"] = _SURROGATE_RE.sub('\ufffd', text)
+                        found = True
+    return found
+
+
+def _strip_budget_warnings_from_history(messages: list) -> None:
+    """Remove budget pressure warnings from tool-result messages in-place.
+
+    Budget warnings are turn-scoped signals that must not leak into replayed
+    history.  They live in tool-result ``content`` either as a JSON key
+    (``_budget_warning``) or appended plain text.
+    """
+    for msg in messages:
+        if not isinstance(msg, dict) or msg.get("role") != "tool":
+            continue
+        content = msg.get("content")
+        if not isinstance(content, str) or "_budget_warning" not in content and "[BUDGET" not in content:
+            continue
+
+        # Try JSON first (the common case: _budget_warning key in a dict)
+        try:
+            parsed = json.loads(content)
+            if isinstance(parsed, dict) and "_budget_warning" in parsed:
+                del parsed["_budget_warning"]
+                msg["content"] = json.dumps(parsed, ensure_ascii=False)
+                continue
+        except (json.JSONDecodeError, TypeError):
+            pass
+
+        # Fallback: strip the text pattern from plain-text tool results
+        cleaned = _BUDGET_WARNING_RE.sub("", content).strip()
+        if cleaned != content:
+            msg["content"] = cleaned
+
+
 class AIAgent:
    """
    AI Agent with tool calling capabilities.
@@ -486,6 +570,7 @@ class AIAgent:
        # instead of going directly to stdout where patch_stdout's StdoutProxy
        # would mangle the escape sequences.  None = use builtins.print.
        self._print_fn = None
+        self.background_review_callback = None  # Optional sync callback for gateway delivery
        self.skip_context_files = skip_context_files
        self.pass_session_id = pass_session_id
        self.log_prefix_chars = log_prefix_chars
@@ -533,6 +618,7 @@ class AIAgent:
        self.tool_progress_callback = tool_progress_callback
        self.thinking_callback = thinking_callback
        self.reasoning_callback = reasoning_callback
+        self._reasoning_deltas_fired = False  # Set by _fire_reasoning_delta, reset per API call
        self.clarify_callback = clarify_callback
        self.step_callback = step_callback
        self.stream_delta_callback = stream_delta_callback
@@ -775,6 +861,25 @@ class AIAgent:
                    }
            
            self._client_kwargs = client_kwargs  # stored for rebuilding after interrupt
+
+            # Enable fine-grained tool streaming for Claude on OpenRouter.
+            # Without this, Anthropic buffers the entire tool call and goes
+            # silent for minutes while thinking — OpenRouter's upstream proxy
+            # times out during the silence.  The beta header makes Anthropic
+            # stream tool call arguments token-by-token, keeping the
+            # connection alive.
+            _effective_base = str(client_kwargs.get("base_url", "")).lower()
+            if "openrouter" in _effective_base and "claude" in (self.model or "").lower():
+                headers = client_kwargs.get("default_headers") or {}
+                existing_beta = headers.get("x-anthropic-beta", "")
+                _FINE_GRAINED = "fine-grained-tool-streaming-2025-05-14"
+                if _FINE_GRAINED not in existing_beta:
+                    if existing_beta:
+                        headers["x-anthropic-beta"] = f"{existing_beta},{_FINE_GRAINED}"
+                    else:
+                        headers["x-anthropic-beta"] = _FINE_GRAINED
+                    client_kwargs["default_headers"] = headers
+
            self.api_key = client_kwargs.get("api_key", "")
            try:
                self.client = self._create_openai_client(client_kwargs, reason="agent_init", shared=True)
@@ -979,8 +1084,8 @@ class AIAgent:
                    else:
                        if not hcfg.enabled:
                            logger.debug("Honcho disabled in global config")
-                        elif not hcfg.api_key:
-                            logger.debug("Honcho enabled but no API key configured")
+                        elif not (hcfg.api_key or hcfg.base_url):
+                            logger.debug("Honcho enabled but no API key or base URL configured")
                        else:
                            logger.debug("Honcho enabled but missing API key or disabled in config")
            except Exception as e:
@@ -1017,6 +1122,13 @@ class AIAgent:
        except Exception:
            pass

+        # Tool-use enforcement config: "auto" (default — matches hardcoded
+        # model list), true (always), false (never), or list of substrings.
+        _agent_section = _agent_cfg.get("agent", {})
+        if not isinstance(_agent_section, dict):
+            _agent_section = {}
+        self._tool_use_enforcement = _agent_section.get("tool_use_enforcement", "auto")
+
        # Initialize context compressor for automatic context management
        # Compresses conversation when approaching model's context limit
        # Configuration via config.yaml (compression section)
@@ -1525,6 +1637,12 @@ class AIAgent:
                if actions:
                    summary = " · ".join(dict.fromkeys(actions))
                    self._safe_print(f"  💾 {summary}")
+                    _bg_cb = self.background_review_callback
+                    if _bg_cb:
+                        try:
+                            _bg_cb(f"💾 {summary}")
+                        except Exception:
+                            pass

            except Exception as e:
                logger.debug("Background memory/skill review failed: %s", e)
@@ -2048,6 +2166,23 @@ class AIAgent:
                    msg["content"] = self._clean_session_content(msg["content"])
                cleaned.append(msg)

+            # Guard: never overwrite a larger session log with fewer messages.
+            # This protects against data loss when --resume loads a session whose
+            # messages weren't fully written to SQLite — the resumed agent starts
+            # with partial history and would otherwise clobber the full JSON log.
+            if self.session_log_file.exists():
+                try:
+                    existing = json.loads(self.session_log_file.read_text(encoding="utf-8"))
+                    existing_count = existing.get("message_count", len(existing.get("messages", [])))
+                    if existing_count > len(cleaned):
+                        logging.debug(
+                            "Skipping session log overwrite: existing has %d messages, current has %d",
+                            existing_count, len(cleaned),
+                        )
+                        return
+                except Exception:
+                    pass  # corrupted existing file — allow the overwrite
+
            entry = {
                "session_id": self.session_id,
                "model": self.model,
@@ -2157,8 +2292,14 @@ class AIAgent:
    # ── Honcho integration helpers ──

    def _honcho_should_activate(self, hcfg) -> bool:
-        """Return True when remote Honcho should be active."""
-        if not hcfg or not hcfg.enabled or not hcfg.api_key:
+        """Return True when Honcho should be active.
+
+        Self-hosted Honcho may be configured with a base_url and no API key,
+        so activation should accept either credential style.
+        """
+        if not hcfg or not hcfg.enabled:
+            return False
+        if not (hcfg.api_key or hcfg.base_url):
            return False
        return True

@@ -2424,6 +2565,30 @@ class AIAgent:
        if tool_guidance:
            prompt_parts.append(" ".join(tool_guidance))

+        # Tool-use enforcement: tells the model to actually call tools instead
+        # of describing intended actions.  Controlled by config.yaml
+        # agent.tool_use_enforcement:
+        #   "auto" (default) — matches TOOL_USE_ENFORCEMENT_MODELS
+        #   true  — always inject (all models)
+        #   false — never inject
+        #   list  — custom model-name substrings to match
+        if self.valid_tool_names:
+            _enforce = self._tool_use_enforcement
+            _inject = False
+            if _enforce is True or (isinstance(_enforce, str) and _enforce.lower() in ("true", "always", "yes", "on")):
+                _inject = True
+            elif _enforce is False or (isinstance(_enforce, str) and _enforce.lower() in ("false", "never", "no", "off")):
+                _inject = False
+            elif isinstance(_enforce, list):
+                model_lower = (self.model or "").lower()
+                _inject = any(p.lower() in model_lower for p in _enforce if isinstance(p, str))
+            else:
+                # "auto" or any unrecognised value — use hardcoded defaults
+                model_lower = (self.model or "").lower()
+                _inject = any(p in model_lower for p in TOOL_USE_ENFORCEMENT_MODELS)
+            if _inject:
+                prompt_parts.append(TOOL_USE_ENFORCEMENT_GUIDANCE)
+
        # Honcho CLI awareness: tell Hermes about its own management commands
        # so it can refer the user to them rather than reinventing answers.
        if self._honcho and self._honcho_session_key:
@@ -2496,7 +2661,13 @@ class AIAgent:

        has_skills_tools = any(name in self.valid_tool_names for name in ['skills_list', 'skill_view', 'skill_manage'])
        if has_skills_tools:
-            avail_toolsets = {ts for ts, avail in check_toolset_requirements().items() if avail}
+            avail_toolsets = {
+                toolset
+                for toolset in (
+                    get_toolset_for_tool(tool_name) for tool_name in self.valid_tool_names
+                )
+                if toolset
+            }
            skills_prompt = build_skills_system_prompt(
                available_tools=self.valid_tool_names,
                available_toolsets=avail_toolsets,
@@ -3380,6 +3551,7 @@ class AIAgent:
        max_stream_retries = 1
        has_tool_calls = False
        first_delta_fired = False
+        self._reasoning_deltas_fired = False
        for attempt in range(max_stream_retries + 1):
            try:
                with active_client.responses.stream(**api_kwargs) as stream:
@@ -3656,6 +3828,7 @@ class AIAgent:

    def _fire_reasoning_delta(self, text: str) -> None:
        """Fire reasoning callback if registered."""
+        self._reasoning_deltas_fired = True
        cb = self.reasoning_callback
        if cb is not None:
            try:
@@ -3734,7 +3907,7 @@ class AIAgent:
        def _call_chat_completions():
            """Stream a chat completions response."""
            import httpx as _httpx
-            _base_timeout = float(os.getenv("HERMES_API_TIMEOUT", 900.0))
+            _base_timeout = float(os.getenv("HERMES_API_TIMEOUT", 1800.0))
            _stream_read_timeout = float(os.getenv("HERMES_STREAM_READ_TIMEOUT", 60.0))
            stream_kwargs = {
                **api_kwargs,
@@ -3750,16 +3923,28 @@ class AIAgent:
            request_client_holder["client"] = self._create_request_openai_client(
                reason="chat_completion_stream_request"
            )
+            # Reset stale-stream timer so the detector measures from this
+            # attempt's start, not a previous attempt's last chunk.
+            last_chunk_time["t"] = time.time()
            stream = request_client_holder["client"].chat.completions.create(**stream_kwargs)

            content_parts: list = []
            tool_calls_acc: dict = {}
            tool_gen_notified: set = set()
+            # Ollama-compatible endpoints reuse index 0 for every tool call
+            # in a parallel batch, distinguishing them only by id.  Track
+            # the last seen id per raw index so we can detect a new tool
+            # call starting at the same index and redirect it to a fresh slot.
+            _last_id_at_idx: dict = {}      # raw_index -> last seen non-empty id
+            _active_slot_by_idx: dict = {}  # raw_index -> current slot in tool_calls_acc
            finish_reason = None
            model_name = None
            role = "assistant"
            reasoning_parts: list = []
            usage_obj = None
+            # Reset per-call reasoning tracking so _build_assistant_message
+            # knows whether reasoning was already displayed during streaming.
+            self._reasoning_deltas_fired = False

            for chunk in stream:
                last_chunk_time["t"] = time.time()
@@ -3793,11 +3978,45 @@ class AIAgent:
                        _fire_first_delta()
                        self._fire_stream_delta(delta.content)
                        deltas_were_sent["yes"] = True
+                    else:
+                        # Tool calls suppress regular content streaming (avoids
+                        # displaying chatty "I'll use the tool..." text alongside
+                        # tool calls).  But reasoning tags embedded in suppressed
+                        # content should still reach the display — otherwise the
+                        # reasoning box only appears as a post-response fallback,
+                        # rendering it confusingly after the already-streamed
+                        # response.  Route suppressed content through the stream
+                        # delta callback so its tag extraction can fire the
+                        # reasoning display.  Non-reasoning text is harmlessly
+                        # suppressed by the CLI's _stream_delta when the stream
+                        # box is already closed (tool boundary flush).
+                        if self.stream_delta_callback:
+                            try:
+                                self.stream_delta_callback(delta.content)
+                            except Exception:
+                                pass

                # Accumulate tool call deltas — notify display on first name
                if delta and delta.tool_calls:
                    for tc_delta in delta.tool_calls:
-                        idx = tc_delta.index if tc_delta.index is not None else 0
+                        raw_idx = tc_delta.index if tc_delta.index is not None else 0
+                        delta_id = tc_delta.id or ""
+
+                        # Ollama fix: detect a new tool call reusing the same
+                        # raw index (different id) and redirect to a fresh slot.
+                        if raw_idx not in _active_slot_by_idx:
+                            _active_slot_by_idx[raw_idx] = raw_idx
+                        if (
+                            delta_id
+                            and raw_idx in _last_id_at_idx
+                            and delta_id != _last_id_at_idx[raw_idx]
+                        ):
+                            new_slot = max(tool_calls_acc, default=-1) + 1
+                            _active_slot_by_idx[raw_idx] = new_slot
+                        if delta_id:
+                            _last_id_at_idx[raw_idx] = delta_id
+                        idx = _active_slot_by_idx[raw_idx]
+
                        if idx not in tool_calls_acc:
                            tool_calls_acc[idx] = {
                                "id": tc_delta.id or "",
@@ -3879,7 +4098,10 @@ class AIAgent:
            works unchanged.
            """
            has_tool_use = False
+            self._reasoning_deltas_fired = False

+            # Reset stale-stream timer for this attempt
+            last_chunk_time["t"] = time.time()
            # Use the Anthropic SDK's streaming context manager
            with self._anthropic_client.messages.stream(**api_kwargs) as stream:
                for event in stream:
@@ -3947,7 +4169,37 @@ class AIAgent:
                            e, (_httpx.ConnectError, _httpx.RemoteProtocolError, ConnectionError)
                        )

-                        if _is_timeout or _is_conn_err:
+                        # SSE error events from proxies (e.g. OpenRouter sends
+                        # {"error":{"message":"Network connection lost."}}) are
+                        # raised as APIError by the OpenAI SDK.  These are
+                        # semantically identical to httpx connection drops —
+                        # the upstream stream died — and should be retried with
+                        # a fresh connection.  Distinguish from HTTP errors:
+                        # APIError from SSE has no status_code, while
+                        # APIStatusError (4xx/5xx) always has one.
+                        _is_sse_conn_err = False
+                        if not _is_timeout and not _is_conn_err:
+                            from openai import APIError as _APIError
+                            if isinstance(e, _APIError) and not getattr(e, "status_code", None):
+                                _err_lower_sse = str(e).lower()
+                                _SSE_CONN_PHRASES = (
+                                    "connection lost",
+                                    "connection reset",
+                                    "connection closed",
+                                    "connection terminated",
+                                    "network error",
+                                    "network connection",
+                                    "terminated",
+                                    "peer closed",
+                                    "broken pipe",
+                                    "upstream connect error",
+                                )
+                                _is_sse_conn_err = any(
+                                    phrase in _err_lower_sse
+                                    for phrase in _SSE_CONN_PHRASES
+                                )
+
+                        if _is_timeout or _is_conn_err or _is_sse_conn_err:
                            # Transient network / timeout error. Retry the
                            # streaming request with a fresh connection first.
                            if _stream_attempt < _max_stream_retries:
@@ -3992,6 +4244,10 @@ class AIAgent:
                            )

                        try:
+                            # Reset stale timer — the non-streaming fallback
+                            # uses its own client; prevent the stale detector
+                            # from firing on stale timestamps from failed streams.
+                            last_chunk_time["t"] = time.time()
                            result["response"] = self._interruptible_api_call(api_kwargs)
                        except Exception as fallback_err:
                            result["error"] = fallback_err
@@ -4001,7 +4257,19 @@ class AIAgent:
                if request_client is not None:
                    self._close_request_openai_client(request_client, reason="stream_request_complete")

-        _stream_stale_timeout = float(os.getenv("HERMES_STREAM_STALE_TIMEOUT", 90.0))
+        _stream_stale_timeout_base = float(os.getenv("HERMES_STREAM_STALE_TIMEOUT", 180.0))
+        # Scale the stale timeout for large contexts: slow models (like Opus)
+        # can legitimately think for minutes before producing the first token
+        # when the context is large.  Without this, the stale detector kills
+        # healthy connections during the model's thinking phase, producing
+        # spurious RemoteProtocolError ("peer closed connection").
+        _est_tokens = sum(len(str(v)) for v in api_kwargs.get("messages", [])) // 4
+        if _est_tokens > 100_000:
+            _stream_stale_timeout = max(_stream_stale_timeout_base, 300.0)
+        elif _est_tokens > 50_000:
+            _stream_stale_timeout = max(_stream_stale_timeout_base, 240.0)
+        else:
+            _stream_stale_timeout = _stream_stale_timeout_base

        t = threading.Thread(target=_call, daemon=True)
        t.start()
@@ -4127,6 +4395,25 @@ class AIAgent:
                or is_native_anthropic
            )

+            # Update context compressor limits for the fallback model.
+            # Without this, compression decisions use the primary model's
+            # context window (e.g. 200K) instead of the fallback's (e.g. 32K),
+            # causing oversized sessions to overflow the fallback.
+            if hasattr(self, 'context_compressor') and self.context_compressor:
+                from agent.model_metadata import get_model_context_length
+                fb_context_length = get_model_context_length(
+                    self.model, base_url=self.base_url,
+                    api_key=self.api_key, provider=self.provider,
+                )
+                self.context_compressor.model = self.model
+                self.context_compressor.base_url = self.base_url
+                self.context_compressor.api_key = self.api_key
+                self.context_compressor.provider = self.provider
+                self.context_compressor.context_length = fb_context_length
+                self.context_compressor.threshold_tokens = int(
+                    fb_context_length * self.context_compressor.threshold_percent
+                )
+
            self._emit_status(
                f"🔄 Primary model failed — switching to fallback: "
                f"{fb_model} via {fb_provider}"
@@ -4296,6 +4583,10 @@ class AIAgent:
        if self.api_mode == "anthropic_messages":
            from agent.anthropic_adapter import build_anthropic_kwargs
            anthropic_messages = self._prepare_anthropic_messages_for_api(api_messages)
+            # Pass context_length so the adapter can clamp max_tokens if the
+            # user configured a smaller context window than the model's output limit.
+            ctx_len = getattr(self, "context_compressor", None)
+            ctx_len = ctx_len.context_length if ctx_len else None
            return build_anthropic_kwargs(
                model=self.model,
                messages=anthropic_messages,
@@ -4304,6 +4595,7 @@ class AIAgent:
                reasoning_config=self.reasoning_config,
                is_oauth=self._is_anthropic_oauth,
                preserve_dots=self._anthropic_preserve_dots(),
+                context_length=ctx_len,
            )

        if self.api_mode == "codex_responses":
@@ -4415,11 +4707,25 @@ class AIAgent:
            "model": self.model,
            "messages": sanitized_messages,
            "tools": self.tools if self.tools else None,
-            "timeout": float(os.getenv("HERMES_API_TIMEOUT", 900.0)),
+            "timeout": float(os.getenv("HERMES_API_TIMEOUT", 1800.0)),
        }

        if self.max_tokens is not None:
            api_kwargs.update(self._max_tokens_param(self.max_tokens))
+        elif self._is_openrouter_url() and "claude" in (self.model or "").lower():
+            # OpenRouter translates requests to Anthropic's Messages API,
+            # which requires max_tokens as a mandatory field.  When we omit
+            # it, OpenRouter picks a default that can be too low — the model
+            # spends its output budget on thinking and has almost nothing
+            # left for the actual response (especially large tool calls like
+            # write_file).  Sending the model's real output limit ensures
+            # full capacity.  Other providers handle the default fine.
+            try:
+                from agent.anthropic_adapter import _get_anthropic_max_output
+                _model_output_limit = _get_anthropic_max_output(self.model)
+                api_kwargs["max_tokens"] = _model_output_limit
+            except Exception:
+                pass  # fail open — let OpenRouter pick its default

        extra_body = {}

@@ -4555,11 +4861,15 @@ class AIAgent:
            logging.debug(f"Captured reasoning ({len(reasoning_text)} chars): {reasoning_text}")

        if reasoning_text and self.reasoning_callback:
-            # Skip callback for <think>-extracted reasoning when streaming is active.
-            # _stream_delta() already displayed <think> blocks during streaming;
-            # firing the callback again would cause duplicate display.
-            # Structured reasoning (from reasoning_content field) always fires.
-            if _from_structured or not self.stream_delta_callback:
+            # Skip callback when streaming is active — reasoning was already
+            # displayed during the stream via one of two paths:
+            #   (a) _fire_reasoning_delta (structured reasoning_content deltas)
+            #   (b) _stream_delta tag extraction (<think>/<REASONING_SCRATCHPAD>)
+            # When streaming is NOT active, always fire so non-streaming modes
+            # (gateway, batch, quiet) still get reasoning.
+            # Any reasoning that wasn't shown during streaming is caught by the
+            # CLI post-response display fallback (cli.py _reasoning_shown_this_turn).
+            if not self.stream_delta_callback:
                try:
                    self.reasoning_callback(reasoning_text)
                except Exception:
@@ -5080,7 +5390,7 @@ class AIAgent:
        spinner = None
        if self.quiet_mode and not self.tool_progress_callback:
            face = random.choice(KawaiiSpinner.KAWAII_WAITING)
-            spinner = KawaiiSpinner(f"{face} ⚡ running {num_tools} tools concurrently", spinner_type='dots')
+            spinner = KawaiiSpinner(f"{face} ⚡ running {num_tools} tools concurrently", spinner_type='dots', print_fn=self._print_fn)
            spinner.start()

        try:
@@ -5121,7 +5431,7 @@ class AIAgent:
            # Print cute message per tool
            if self.quiet_mode:
                cute_msg = _get_cute_tool_message_impl(name, args, tool_duration, result=function_result)
-                print(f"  {cute_msg}")
+                self._safe_print(f"  {cute_msg}")
            elif not self.quiet_mode:
                if self.verbose_logging:
                    print(f"  ✅ Tool {i+1} completed in {tool_duration:.2f}s")
@@ -5306,7 +5616,7 @@ class AIAgent:
                spinner = None
                if self.quiet_mode and not self.tool_progress_callback:
                    face = random.choice(KawaiiSpinner.KAWAII_WAITING)
-                    spinner = KawaiiSpinner(f"{face} {spinner_label}", spinner_type='dots')
+                    spinner = KawaiiSpinner(f"{face} {spinner_label}", spinner_type='dots', print_fn=self._print_fn)
                    spinner.start()
                self._delegate_spinner = spinner
                _delegate_result = None
@@ -5336,7 +5646,7 @@ class AIAgent:
                    preview = _build_tool_preview(function_name, function_args) or function_name
                    if len(preview) > 30:
                        preview = preview[:27] + "..."
-                    spinner = KawaiiSpinner(f"{face} {emoji} {preview}", spinner_type='dots')
+                    spinner = KawaiiSpinner(f"{face} {emoji} {preview}", spinner_type='dots', print_fn=self._print_fn)
                    spinner.start()
                _spinner_result = None
                try:
@@ -5697,6 +6007,14 @@ class AIAgent:
        # Installed once, transparent when streams are healthy, prevents crash on write.
        _install_safe_stdio()

+        # Sanitize surrogate characters from user input.  Clipboard paste from
+        # rich-text editors (Google Docs, Word, etc.) can inject lone surrogates
+        # that are invalid UTF-8 and crash JSON serialization in the OpenAI SDK.
+        if isinstance(user_message, str):
+            user_message = _sanitize_surrogates(user_message)
+        if isinstance(persist_user_message, str):
+            persist_user_message = _sanitize_surrogates(persist_user_message)
+
        # Store stream callback for _interruptible_api_call to pick up
        self._stream_callback = stream_callback
        self._persist_user_message_idx = None
@@ -5713,6 +6031,7 @@ class AIAgent:
        self._codex_incomplete_retries = 0
        self._last_content_with_tools = None
        self._mute_post_response = False
+        self._surrogate_sanitized = False
        # NOTE: _turns_since_memory and _iters_since_skill are NOT reset here.
        # They are initialized in __init__ and must persist across run_conversation
        # calls so that nudge logic accumulates correctly in CLI mode.
@@ -5720,6 +6039,14 @@ class AIAgent:
        
        # Initialize conversation (copy to avoid mutating the caller's list)
        messages = list(conversation_history) if conversation_history else []
+
+        # Strip budget pressure warnings from previous turns.  These are
+        # turn-scoped signals injected by _get_budget_warning() into tool
+        # result content.  If left in the replayed history, models (especially
+        # GPT-family) interpret them as still-active instructions and avoid
+        # making tool calls in ALL subsequent turns.
+        if messages:
+            _strip_budget_warnings_from_history(messages)
        
        # Hydrate todo store from conversation history (gateway creates a fresh
        # AIAgent per message, so the in-memory store is empty -- we need to
@@ -5815,6 +6142,22 @@ class AIAgent:
                    self._cached_system_prompt = (
                        self._cached_system_prompt + "\n\n" + self._honcho_context
                    ).strip()
+
+                # Plugin hook: on_session_start
+                # Fired once when a brand-new session is created (not on
+                # continuation).  Plugins can use this to initialise
+                # session-scoped state (e.g. warm a memory cache).
+                try:
+                    from hermes_cli.plugins import invoke_hook as _invoke_hook
+                    _invoke_hook(
+                        "on_session_start",
+                        session_id=self.session_id,
+                        model=self.model,
+                        platform=getattr(self, "platform", None) or "",
+                    )
+                except Exception as exc:
+                    logger.warning("on_session_start hook failed: %s", exc)
+
                # Store the system prompt snapshot in SQLite
                if self._session_db:
                    try:
@@ -5876,6 +6219,34 @@ class AIAgent:
                    if _preflight_tokens < self.context_compressor.threshold_tokens:
                        break  # Under threshold

+        # Plugin hook: pre_llm_call
+        # Fired once per turn before the tool-calling loop.  Plugins can
+        # return a dict with a ``context`` key whose value is a string
+        # that will be appended to the ephemeral system prompt for every
+        # API call in this turn (not persisted to session DB or cache).
+        _plugin_turn_context = ""
+        try:
+            from hermes_cli.plugins import invoke_hook as _invoke_hook
+            _pre_results = _invoke_hook(
+                "pre_llm_call",
+                session_id=self.session_id,
+                user_message=original_user_message,
+                conversation_history=list(messages),
+                is_first_turn=(not bool(conversation_history)),
+                model=self.model,
+                platform=getattr(self, "platform", None) or "",
+            )
+            _ctx_parts = []
+            for r in _pre_results:
+                if isinstance(r, dict) and r.get("context"):
+                    _ctx_parts.append(str(r["context"]))
+                elif isinstance(r, str) and r.strip():
+                    _ctx_parts.append(r)
+            if _ctx_parts:
+                _plugin_turn_context = "\n\n".join(_ctx_parts)
+        except Exception as exc:
+            logger.warning("pre_llm_call hook failed: %s", exc)
+
        # Main conversation loop
        api_call_count = 0
        final_response = None
@@ -5973,6 +6344,9 @@ class AIAgent:
            effective_system = active_system_prompt or ""
            if self.ephemeral_system_prompt:
                effective_system = (effective_system + "\n\n" + self.ephemeral_system_prompt).strip()
+            # Plugin context from pre_llm_call hooks — ephemeral, not cached.
+            if _plugin_turn_context:
+                effective_system = (effective_system + "\n\n" + _plugin_turn_context).strip()
            if effective_system:
                api_messages = [{"role": "system", "content": effective_system}] + api_messages

@@ -6019,7 +6393,7 @@ class AIAgent:
                    # Raw KawaiiSpinner only when no streaming consumers
                    # (would conflict with streamed token output)
                    spinner_type = random.choice(['brain', 'sparkle', 'pulse', 'moon', 'star'])
-                    thinking_spinner = KawaiiSpinner(f"{face} {verb}...", spinner_type=spinner_type)
+                    thinking_spinner = KawaiiSpinner(f"{face} {verb}...", spinner_type=spinner_type, print_fn=self._print_fn)
                    thinking_spinner.start()
            
            # Log request details if verbose
@@ -6249,6 +6623,62 @@ class AIAgent:
                    if finish_reason == "length":
                        self._vprint(f"{self.log_prefix}⚠️  Response truncated (finish_reason='length') - model hit max output tokens", force=True)

+                        # ── Detect thinking-budget exhaustion ──────────────
+                        # When the model spends ALL output tokens on reasoning
+                        # and has none left for the response, continuation
+                        # retries are pointless.  Detect this early and give a
+                        # targeted error instead of wasting 3 API calls.
+                        _trunc_content = None
+                        if self.api_mode == "chat_completions":
+                            _trunc_msg = response.choices[0].message if (hasattr(response, "choices") and response.choices) else None
+                            _trunc_content = getattr(_trunc_msg, "content", None) if _trunc_msg else None
+                        elif self.api_mode == "anthropic_messages":
+                            # Anthropic response.content is a list of blocks
+                            _text_parts = []
+                            for _blk in getattr(response, "content", []):
+                                if getattr(_blk, "type", None) == "text":
+                                    _text_parts.append(getattr(_blk, "text", ""))
+                            _trunc_content = "\n".join(_text_parts) if _text_parts else None
+
+                        _thinking_exhausted = (
+                            _trunc_content is not None
+                            and not self._has_content_after_think_block(_trunc_content)
+                        ) or _trunc_content is None
+
+                        if _thinking_exhausted:
+                            _exhaust_error = (
+                                "Model used all output tokens on reasoning with none left "
+                                "for the response. Try lowering reasoning effort or "
+                                "increasing max_tokens."
+                            )
+                            self._vprint(
+                                f"{self.log_prefix}💭 Reasoning exhausted the output token budget — "
+                                f"no visible response was produced.",
+                                force=True,
+                            )
+                            # Return a user-friendly message as the response so
+                            # CLI (response box) and gateway (chat message) both
+                            # display it naturally instead of a suppressed error.
+                            _exhaust_response = (
+                                "⚠️ **Thinking Budget Exhausted**\n\n"
+                                "The model used all its output tokens on reasoning "
+                                "and had none left for the actual response.\n\n"
+                                "To fix this:\n"
+                                "→ Lower reasoning effort: `/thinkon low` or `/thinkon minimal`\n"
+                                "→ Increase the output token limit: "
+                                "set `model.max_tokens` in config.yaml"
+                            )
+                            self._cleanup_task_resources(effective_task_id)
+                            self._persist_session(messages, conversation_history)
+                            return {
+                                "final_response": _exhaust_response,
+                                "messages": messages,
+                                "api_calls": api_call_count,
+                                "completed": False,
+                                "partial": True,
+                                "error": _exhaust_error,
+                            }
+
                        if self.api_mode == "chat_completions":
                            assistant_message = response.choices[0].message
                            if not assistant_message.tool_calls:
@@ -6437,6 +6867,24 @@ class AIAgent:
                    if self.thinking_callback:
                        self.thinking_callback("")

+                    # -----------------------------------------------------------
+                    # Surrogate character recovery.  UnicodeEncodeError happens
+                    # when the messages contain lone surrogates (U+D800..U+DFFF)
+                    # that are invalid UTF-8.  Common source: clipboard paste
+                    # from Google Docs or similar rich-text editors.  We sanitize
+                    # the entire messages list in-place and retry once.
+                    # -----------------------------------------------------------
+                    if isinstance(api_error, UnicodeEncodeError) and not getattr(self, '_surrogate_sanitized', False):
+                        self._surrogate_sanitized = True
+                        if _sanitize_messages_surrogates(messages):
+                            self._vprint(
+                                f"{self.log_prefix}⚠️  Stripped invalid surrogate characters from messages. Retrying...",
+                                force=True,
+                            )
+                            continue
+                        # Surrogates weren't in messages — might be in system
+                        # prompt or prefill.  Fall through to normal error path.
+
                    status_code = getattr(api_error, "status_code", None)
                    if (
                        self.api_mode == "codex_responses"
@@ -6705,8 +7153,13 @@ class AIAgent:
                    # 529 (Anthropic overloaded) is also transient.
                    # Also catch local validation errors (ValueError, TypeError) — these
                    # are programming bugs, not transient failures.
+                    # Exclude UnicodeEncodeError — it's a ValueError subclass but is
+                    # handled separately by the surrogate sanitization path above.
                    _RETRYABLE_STATUS_CODES = {413, 429, 529}
-                    is_local_validation_error = isinstance(api_error, (ValueError, TypeError))
+                    is_local_validation_error = (
+                        isinstance(api_error, (ValueError, TypeError))
+                        and not isinstance(api_error, UnicodeEncodeError)
+                    )
                    # Detect generic 400s from Anthropic OAuth (transient server-side failures).
                    # Real invalid_request_error responses include a descriptive message;
                    # transient ones contain only "Error" or are empty. (ref: issue #1608)
@@ -6776,6 +7229,36 @@ class AIAgent:
                        _final_summary = self._summarize_api_error(api_error)
                        self._vprint(f"{self.log_prefix}❌ Max retries ({max_retries}) exceeded. Giving up.", force=True)
                        self._vprint(f"{self.log_prefix}   💀 Final error: {_final_summary}", force=True)
+
+                        # Detect SSE stream-drop pattern (e.g. "Network
+                        # connection lost") and surface actionable guidance.
+                        # This typically happens when the model generates a
+                        # very large tool call (write_file with huge content)
+                        # and the proxy/CDN drops the stream mid-response.
+                        _is_stream_drop = (
+                            not getattr(api_error, "status_code", None)
+                            and any(p in error_msg for p in (
+                                "connection lost", "connection reset",
+                                "connection closed", "network connection",
+                                "network error", "terminated",
+                            ))
+                        )
+                        if _is_stream_drop:
+                            self._vprint(
+                                f"{self.log_prefix}   💡 The provider's stream "
+                                f"connection keeps dropping. This often happens "
+                                f"when the model tries to write a very large "
+                                f"file in a single tool call.",
+                                force=True,
+                            )
+                            self._vprint(
+                                f"{self.log_prefix}      Try asking the model "
+                                f"to use execute_code with Python's open() for "
+                                f"large files, or to write the file in smaller "
+                                f"sections.",
+                                force=True,
+                            )
+
                        logging.error(
                            "%sAPI call failed after %s retries. %s | provider=%s model=%s msgs=%s tokens=~%s",
                            self.log_prefix, max_retries, _final_summary,
@@ -6785,8 +7268,18 @@ class AIAgent:
                            api_kwargs, reason="max_retries_exhausted", error=api_error,
                        )
                        self._persist_session(messages, conversation_history)
+                        _final_response = f"API call failed after {max_retries} retries: {_final_summary}"
+                        if _is_stream_drop:
+                            _final_response += (
+                                "\n\nThe provider's stream connection keeps "
+                                "dropping — this often happens when generating "
+                                "very large tool call responses (e.g. write_file "
+                                "with long content). Try asking me to use "
+                                "execute_code with Python's open() for large "
+                                "files, or to write in smaller sections."
+                            )
                        return {
-                            "final_response": f"API call failed after {max_retries} retries: {_final_summary}",
+                            "final_response": _final_response,
                            "messages": messages,
                            "api_calls": api_call_count,
                            "completed": False,
@@ -7164,7 +7657,6 @@ class AIAgent:
                        except Exception:
                            pass

-                    _msg_count_before_tools = len(messages)
                    self._execute_tool_calls(assistant_message, messages, effective_task_id, api_call_count)

                    # Signal that a paragraph break is needed before the next
@@ -7182,18 +7674,18 @@ class AIAgent:
                    if _tc_names == {"execute_code"}:
                        self.iteration_budget.refund()
                    
-                    # Estimate next prompt size using real token counts from the
-                    # last API response + rough estimate of newly appended tool
-                    # results.  This catches cases where tool results push the
-                    # context past the limit that last_prompt_tokens alone misses
-                    # (e.g. large file reads, web extractions).
+                    # Use real token counts from the API response to decide
+                    # compression.  prompt_tokens + completion_tokens is the
+                    # actual context size the provider reported plus the
+                    # assistant turn — a tight lower bound for the next prompt.
+                    # Tool results appended above aren't counted yet, but the
+                    # threshold (default 50%) leaves ample headroom; if tool
+                    # results push past it, the next API call will report the
+                    # real total and trigger compression then.
                    _compressor = self.context_compressor
-                    _new_tool_msgs = messages[_msg_count_before_tools:]
-                    _new_chars = sum(len(str(m.get("content", "") or "")) for m in _new_tool_msgs)
-                    _estimated_next_prompt = (
+                    _real_tokens = (
                        _compressor.last_prompt_tokens
                        + _compressor.last_completion_tokens
-                        + _new_chars // 3  # conservative: JSON-heavy tool results ≈ 3 chars/token
                    )

                    # ── Context pressure warnings (user-facing only) ──────────
@@ -7203,12 +7695,12 @@ class AIAgent:
                    # Does not inject into messages — just prints to CLI output
                    # and fires status_callback for gateway platforms.
                    if _compressor.threshold_tokens > 0:
-                        _compaction_progress = _estimated_next_prompt / _compressor.threshold_tokens
+                        _compaction_progress = _real_tokens / _compressor.threshold_tokens
                        if _compaction_progress >= 0.85 and not self._context_pressure_warned:
                            self._context_pressure_warned = True
                            self._emit_context_pressure(_compaction_progress, _compressor)

-                    if self.compression_enabled and _compressor.should_compress(_estimated_next_prompt):
+                    if self.compression_enabled and _compressor.should_compress(_real_tokens):
                        messages, active_system_prompt = self._compress_context(
                            messages, system_message,
                            approx_tokens=self.context_compressor.last_prompt_tokens,
@@ -7455,6 +7947,25 @@ class AIAgent:
            self._honcho_sync(original_user_message, final_response)
            self._queue_honcho_prefetch(original_user_message)

+        # Plugin hook: post_llm_call
+        # Fired once per turn after the tool-calling loop completes.
+        # Plugins can use this to persist conversation data (e.g. sync
+        # to an external memory system).
+        if final_response and not interrupted:
+            try:
+                from hermes_cli.plugins import invoke_hook as _invoke_hook
+                _invoke_hook(
+                    "post_llm_call",
+                    session_id=self.session_id,
+                    user_message=original_user_message,
+                    assistant_response=final_response,
+                    conversation_history=list(messages),
+                    model=self.model,
+                    platform=getattr(self, "platform", None) or "",
+                )
+            except Exception as exc:
+                logger.warning("post_llm_call hook failed: %s", exc)
+
        # Extract reasoning from the last assistant message (if any)
        last_reasoning = None
        for msg in reversed(messages):
@@ -7520,6 +8031,22 @@ class AIAgent:
            except Exception:
                pass  # Background review is best-effort

+        # Plugin hook: on_session_end
+        # Fired at the very end of every run_conversation call.
+        # Plugins can use this for cleanup, flushing buffers, etc.
+        try:
+            from hermes_cli.plugins import invoke_hook as _invoke_hook
+            _invoke_hook(
+                "on_session_end",
+                session_id=self.session_id,
+                completed=completed,
+                interrupted=interrupted,
+                model=self.model,
+                platform=getattr(self, "platform", None) or "",
+            )
+        except Exception as exc:
+            logger.warning("on_session_end hook failed: %s", exc)
+
        return result

    def chat(self, message: str, stream_callback: Optional[callable] = None) -> str:
@@ -2,7 +2,7 @@
 # Kill all running Modal apps (sandboxes, deployments, etc.)
 #
 # Usage:
-#   bash scripts/kill_modal.sh          # Stop swe-rex (the sandbox app)
+#   bash scripts/kill_modal.sh          # Stop hermes-agent sandboxes
 #   bash scripts/kill_modal.sh --all    # Stop ALL Modal apps

 set -uo pipefail
@@ -17,10 +17,10 @@ if [[ "${1:-}" == "--all" ]]; then
        modal app stop "$app_id" 2>/dev/null || true
    done
 else
-    echo "Stopping swe-rex sandboxes..."
-    APPS=$(echo "$APP_LIST" | grep 'swe-rex' | grep -oE 'ap-[A-Za-z0-9]+' || true)
+    echo "Stopping hermes-agent sandboxes..."
+    APPS=$(echo "$APP_LIST" | grep 'hermes-agent' | grep -oE 'ap-[A-Za-z0-9]+' || true)
    if [[ -z "$APPS" ]]; then
-        echo "  No swe-rex apps found."
+        echo "  No hermes-agent apps found."
    else
        echo "$APPS" | while read app_id; do
            echo "  Stopping $app_id"
@@ -30,5 +30,5 @@ else
 fi

 echo ""
-echo "Current swe-rex status:"
-modal app list 2>/dev/null | grep -E 'State|swe-rex' || echo "  (none)"
+echo "Current hermes-agent status:"
+modal app list 2>/dev/null | grep -E 'State|hermes-agent' || echo "  (none)"
@@ -0,0 +1,180 @@
+---
+name: webhook-subscriptions
+description: Create and manage webhook subscriptions for event-driven agent activation. Use when the user wants external services to trigger agent runs automatically.
+version: 1.0.0
+metadata:
+  hermes:
+    tags: [webhook, events, automation, integrations]
+---
+
+# Webhook Subscriptions
+
+Create dynamic webhook subscriptions so external services (GitHub, GitLab, Stripe, CI/CD, IoT sensors, monitoring tools) can trigger Hermes agent runs by POSTing events to a URL.
+
+## Setup (Required First)
+
+The webhook platform must be enabled before subscriptions can be created. Check with:
+```bash
+hermes webhook list
+```
+
+If it says "Webhook platform is not enabled", set it up:
+
+### Option 1: Setup wizard
+```bash
+hermes gateway setup
+```
+Follow the prompts to enable webhooks, set the port, and set a global HMAC secret.
+
+### Option 2: Manual config
+Add to `~/.hermes/config.yaml`:
+```yaml
+platforms:
+  webhook:
+    enabled: true
+    extra:
+      host: "0.0.0.0"
+      port: 8644
+      secret: "generate-a-strong-secret-here"
+```
+
+### Option 3: Environment variables
+Add to `~/.hermes/.env`:
+```bash
+WEBHOOK_ENABLED=true
+WEBHOOK_PORT=8644
+WEBHOOK_SECRET=generate-a-strong-secret-here
+```
+
+After configuration, start (or restart) the gateway:
+```bash
+hermes gateway run
+# Or if using systemd:
+systemctl --user restart hermes-gateway
+```
+
+Verify it's running:
+```bash
+curl http://localhost:8644/health
+```
+
+## Commands
+
+All management is via the `hermes webhook` CLI command:
+
+### Create a subscription
+```bash
+hermes webhook subscribe <name> \
+  --prompt "Prompt template with {payload.fields}" \
+  --events "event1,event2" \
+  --description "What this does" \
+  --skills "skill1,skill2" \
+  --deliver telegram \
+  --deliver-chat-id "12345" \
+  --secret "optional-custom-secret"
+```
+
+Returns the webhook URL and HMAC secret. The user configures their service to POST to that URL.
+
+### List subscriptions
+```bash
+hermes webhook list
+```
+
+### Remove a subscription
+```bash
+hermes webhook remove <name>
+```
+
+### Test a subscription
+```bash
+hermes webhook test <name>
+hermes webhook test <name> --payload '{"key": "value"}'
+```
+
+## Prompt Templates
+
+Prompts support `{dot.notation}` for accessing nested payload fields:
+
+- `{issue.title}` — GitHub issue title
+- `{pull_request.user.login}` — PR author
+- `{data.object.amount}` — Stripe payment amount
+- `{sensor.temperature}` — IoT sensor reading
+
+If no prompt is specified, the full JSON payload is dumped into the agent prompt.
+
+## Common Patterns
+
+### GitHub: new issues
+```bash
+hermes webhook subscribe github-issues \
+  --events "issues" \
+  --prompt "New GitHub issue #{issue.number}: {issue.title}\n\nAction: {action}\nAuthor: {issue.user.login}\nBody:\n{issue.body}\n\nPlease triage this issue." \
+  --deliver telegram \
+  --deliver-chat-id "-100123456789"
+```
+
+Then in GitHub repo Settings → Webhooks → Add webhook:
+- Payload URL: the returned webhook_url
+- Content type: application/json
+- Secret: the returned secret
+- Events: "Issues"
+
+### GitHub: PR reviews
+```bash
+hermes webhook subscribe github-prs \
+  --events "pull_request" \
+  --prompt "PR #{pull_request.number} {action}: {pull_request.title}\nBy: {pull_request.user.login}\nBranch: {pull_request.head.ref}\n\n{pull_request.body}" \
+  --skills "github-code-review" \
+  --deliver github_comment
+```
+
+### Stripe: payment events
+```bash
+hermes webhook subscribe stripe-payments \
+  --events "payment_intent.succeeded,payment_intent.payment_failed" \
+  --prompt "Payment {data.object.status}: {data.object.amount} cents from {data.object.receipt_email}" \
+  --deliver telegram \
+  --deliver-chat-id "-100123456789"
+```
+
+### CI/CD: build notifications
+```bash
+hermes webhook subscribe ci-builds \
+  --events "pipeline" \
+  --prompt "Build {object_attributes.status} on {project.name} branch {object_attributes.ref}\nCommit: {commit.message}" \
+  --deliver discord \
+  --deliver-chat-id "1234567890"
+```
+
+### Generic monitoring alert
+```bash
+hermes webhook subscribe alerts \
+  --prompt "Alert: {alert.name}\nSeverity: {alert.severity}\nMessage: {alert.message}\n\nPlease investigate and suggest remediation." \
+  --deliver origin
+```
+
+## Security
+
+- Each subscription gets an auto-generated HMAC-SHA256 secret (or provide your own with `--secret`)
+- The webhook adapter validates signatures on every incoming POST
+- Static routes from config.yaml cannot be overwritten by dynamic subscriptions
+- Subscriptions persist to `~/.hermes/webhook_subscriptions.json`
+
+## How It Works
+
+1. `hermes webhook subscribe` writes to `~/.hermes/webhook_subscriptions.json`
+2. The webhook adapter hot-reloads this file on each incoming request (mtime-gated, negligible overhead)
+3. When a POST arrives matching a route, the adapter formats the prompt and triggers an agent run
+4. The agent's response is delivered to the configured target (Telegram, Discord, GitHub comment, etc.)
+
+## Troubleshooting
+
+If webhooks aren't working:
+
+1. **Is the gateway running?** Check with `systemctl --user status hermes-gateway` or `ps aux | grep gateway`
+2. **Is the webhook server listening?** `curl http://localhost:8644/health` should return `{"status": "ok"}`
+3. **Check gateway logs:** `grep webhook ~/.hermes/logs/gateway.log | tail -20`
+4. **Signature mismatch?** Verify the secret in your service matches the one from `hermes webhook list`. GitHub sends `X-Hub-Signature-256`, GitLab sends `X-Gitlab-Token`.
+5. **Firewall/NAT?** The webhook URL must be reachable from the service. For local development, use a tunnel (ngrok, cloudflared).
+6. **Wrong event type?** Check `--events` filter matches what the service sends. Use `hermes webhook test <name>` to verify the route works.
@@ -219,6 +219,9 @@ if command -v gh &>/dev/null && gh auth status &>/dev/null; then
  echo "AUTH_METHOD=gh"
 elif [ -n "$GITHUB_TOKEN" ]; then
  echo "AUTH_METHOD=curl"
+elif [ -f ~/.hermes/.env ] && grep -q "^GITHUB_TOKEN=" ~/.hermes/.env; then
+  export GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" ~/.hermes/.env | head -1 | cut -d= -f2 | tr -d '\n\r')
+  echo "AUTH_METHOD=curl"
 elif grep -q "github.com" ~/.git-credentials 2>/dev/null; then
  export GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
  echo "AUTH_METHOD=curl"
@@ -23,6 +23,11 @@ if command -v gh &>/dev/null && gh auth status &>/dev/null 2>&1; then
    GH_USER=$(gh api user --jq '.login' 2>/dev/null)
 elif [ -n "$GITHUB_TOKEN" ]; then
    GH_AUTH_METHOD="curl"
+elif [ -f "$HOME/.hermes/.env" ] && grep -q "^GITHUB_TOKEN=" "$HOME/.hermes/.env" 2>/dev/null; then
+    GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" "$HOME/.hermes/.env" | head -1 | cut -d= -f2 | tr -d '\n\r')
+    if [ -n "$GITHUB_TOKEN" ]; then
+        GH_AUTH_METHOD="curl"
+    fi
 elif [ -f "$HOME/.git-credentials" ] && grep -q "github.com" "$HOME/.git-credentials" 2>/dev/null; then
    GITHUB_TOKEN=$(grep "github.com" "$HOME/.git-credentials" | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
    if [ -n "$GITHUB_TOKEN" ]; then
@@ -27,7 +27,11 @@ if command -v gh &>/dev/null && gh auth status &>/dev/null; then
 else
  AUTH="git"
  if [ -z "$GITHUB_TOKEN" ]; then
-    GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    if [ -f ~/.hermes/.env ] && grep -q "^GITHUB_TOKEN=" ~/.hermes/.env; then
+      GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" ~/.hermes/.env | head -1 | cut -d= -f2 | tr -d '\n\r')
+    elif grep -q "github.com" ~/.git-credentials 2>/dev/null; then
+      GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    fi
  fi
 fi

@@ -27,7 +27,11 @@ if command -v gh &>/dev/null && gh auth status &>/dev/null; then
 else
  AUTH="git"
  if [ -z "$GITHUB_TOKEN" ]; then
-    GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    if [ -f ~/.hermes/.env ] && grep -q "^GITHUB_TOKEN=" ~/.hermes/.env; then
+      GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" ~/.hermes/.env | head -1 | cut -d= -f2 | tr -d '\n\r')
+    elif grep -q "github.com" ~/.git-credentials 2>/dev/null; then
+      GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    fi
  fi
 fi

@@ -29,7 +29,11 @@ else
  AUTH="git"
  # Ensure we have a token for API calls
  if [ -z "$GITHUB_TOKEN" ]; then
-    GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    if [ -f ~/.hermes/.env ] && grep -q "^GITHUB_TOKEN=" ~/.hermes/.env; then
+      GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" ~/.hermes/.env | head -1 | cut -d= -f2 | tr -d '\n\r')
+    elif grep -q "github.com" ~/.git-credentials 2>/dev/null; then
+      GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    fi
  fi
 fi
 echo "Using: $AUTH"
@@ -26,7 +26,11 @@ if command -v gh &>/dev/null && gh auth status &>/dev/null; then
 else
  AUTH="git"
  if [ -z "$GITHUB_TOKEN" ]; then
-    GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    if [ -f ~/.hermes/.env ] && grep -q "^GITHUB_TOKEN=" ~/.hermes/.env; then
+      GITHUB_TOKEN=$(grep "^GITHUB_TOKEN=" ~/.hermes/.env | head -1 | cut -d= -f2 | tr -d '\n\r')
+    elif grep -q "github.com" ~/.git-credentials 2>/dev/null; then
+      GITHUB_TOKEN=$(grep "github.com" ~/.git-credentials 2>/dev/null | head -1 | sed 's|https://[^:]*:\([^@]*\)@.*|\1|')
+    fi
  fi
 fi

@@ -11,6 +11,7 @@ from agent.auxiliary_client import (
    get_text_auxiliary_client,
    get_vision_auxiliary_client,
    get_available_vision_backends,
+    resolve_vision_provider_client,
    resolve_provider_client,
    auxiliary_max_tokens_param,
    _read_codex_access_token,
@@ -638,6 +639,30 @@ class TestVisionClientFallback:
        assert client.__class__.__name__ == "AnthropicAuxiliaryClient"
        assert model == "claude-haiku-4-5-20251001"

+    def test_selected_codex_provider_short_circuits_vision_auto(self, monkeypatch):
+        def fake_load_config():
+            return {"model": {"provider": "openai-codex", "default": "gpt-5.2-codex"}}
+
+        codex_client = MagicMock()
+        with (
+            patch("hermes_cli.config.load_config", fake_load_config),
+            patch("agent.auxiliary_client._try_codex", return_value=(codex_client, "gpt-5.2-codex")) as mock_codex,
+            patch("agent.auxiliary_client._try_openrouter") as mock_openrouter,
+            patch("agent.auxiliary_client._try_nous") as mock_nous,
+            patch("agent.auxiliary_client._try_anthropic") as mock_anthropic,
+            patch("agent.auxiliary_client._try_custom_endpoint") as mock_custom,
+        ):
+            provider, client, model = resolve_vision_provider_client()
+
+        assert provider == "openai-codex"
+        assert client is codex_client
+        assert model == "gpt-5.2-codex"
+        mock_codex.assert_called_once()
+        mock_openrouter.assert_not_called()
+        mock_nous.assert_not_called()
+        mock_anthropic.assert_not_called()
+        mock_custom.assert_not_called()
+
    def test_vision_auto_includes_codex(self, codex_auth_dir):
        """Codex supports vision (gpt-5.3-codex), so auto mode should use it."""
        with patch("agent.auxiliary_client._read_nous_auth", return_value=None), \
@@ -18,6 +18,8 @@ from agent.prompt_builder import (
    build_context_files_prompt,
    CONTEXT_FILE_MAX_CHARS,
    DEFAULT_AGENT_IDENTITY,
+    TOOL_USE_ENFORCEMENT_GUIDANCE,
+    TOOL_USE_ENFORCEMENT_MODELS,
    MEMORY_GUIDANCE,
    SESSION_SEARCH_GUIDANCE,
    PLATFORM_HINTS,
@@ -232,7 +234,18 @@ class TestPromptBuilderImports:
 # =========================================================================


+import pytest
+
+
 class TestBuildSkillsSystemPrompt:
+    @pytest.fixture(autouse=True)
+    def _clear_skills_cache(self):
+        """Ensure the in-process skills prompt cache doesn't leak between tests."""
+        from agent.prompt_builder import clear_skills_system_prompt_cache
+        clear_skills_system_prompt_cache(clear_snapshot=True)
+        yield
+        clear_skills_system_prompt_cache(clear_snapshot=True)
+
    def test_empty_when_no_skills_dir(self, monkeypatch, tmp_path):
        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
        result = build_skills_system_prompt()
@@ -302,7 +315,7 @@ class TestBuildSkillsSystemPrompt:

        from unittest.mock import patch

-        with patch("tools.skills_tool.sys") as mock_sys:
+        with patch("agent.skill_utils.sys") as mock_sys:
            mock_sys.platform = "darwin"
            result = build_skills_system_prompt()

@@ -330,7 +343,7 @@ class TestBuildSkillsSystemPrompt:
        from unittest.mock import patch

        with patch(
-            "tools.skills_tool._get_disabled_skill_names",
+            "agent.prompt_builder.get_disabled_skill_names",
            return_value={"old-tool"},
        ):
            result = build_skills_system_prompt()
@@ -804,6 +817,13 @@ class TestSkillShouldShow:


 class TestBuildSkillsSystemPromptConditional:
+    @pytest.fixture(autouse=True)
+    def _clear_skills_cache(self):
+        from agent.prompt_builder import clear_skills_system_prompt_cache
+        clear_skills_system_prompt_cache(clear_snapshot=True)
+        yield
+        clear_skills_system_prompt_cache(clear_snapshot=True)
+
    def test_fallback_skill_hidden_when_primary_available(self, monkeypatch, tmp_path):
        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
        skill_dir = tmp_path / "skills" / "search" / "duckduckgo"
@@ -908,3 +928,98 @@ class TestBuildSkillsSystemPromptConditional:
            available_toolsets=set(),
        )
        assert "nested-null" in result
+
+
+# =========================================================================
+# Tool-use enforcement guidance
+# =========================================================================
+
+
+class TestToolUseEnforcementGuidance:
+    def test_guidance_mentions_tool_calls(self):
+        assert "tool call" in TOOL_USE_ENFORCEMENT_GUIDANCE.lower()
+
+    def test_guidance_forbids_description_only(self):
+        assert "describe" in TOOL_USE_ENFORCEMENT_GUIDANCE.lower()
+        assert "promise" in TOOL_USE_ENFORCEMENT_GUIDANCE.lower()
+
+    def test_guidance_requires_action(self):
+        assert "MUST" in TOOL_USE_ENFORCEMENT_GUIDANCE
+
+    def test_enforcement_models_includes_gpt(self):
+        assert "gpt" in TOOL_USE_ENFORCEMENT_MODELS
+
+    def test_enforcement_models_includes_codex(self):
+        assert "codex" in TOOL_USE_ENFORCEMENT_MODELS
+
+    def test_enforcement_models_is_tuple(self):
+        assert isinstance(TOOL_USE_ENFORCEMENT_MODELS, tuple)
+
+
+# =========================================================================
+# Budget warning history stripping
+# =========================================================================
+
+
+class TestStripBudgetWarningsFromHistory:
+    def test_strips_json_budget_warning_key(self):
+        import json
+        from run_agent import _strip_budget_warnings_from_history
+
+        messages = [
+            {"role": "tool", "tool_call_id": "c1", "content": json.dumps({
+                "output": "hello",
+                "exit_code": 0,
+                "_budget_warning": "[BUDGET: Iteration 55/60. 5 iterations left. Start consolidating your work.]",
+            })},
+        ]
+        _strip_budget_warnings_from_history(messages)
+        parsed = json.loads(messages[0]["content"])
+        assert "_budget_warning" not in parsed
+        assert parsed["output"] == "hello"
+        assert parsed["exit_code"] == 0
+
+    def test_strips_text_budget_warning(self):
+        from run_agent import _strip_budget_warnings_from_history
+
+        messages = [
+            {"role": "tool", "tool_call_id": "c1",
+             "content": "some result\n\n[BUDGET WARNING: Iteration 58/60. Only 2 iteration(s) left. Provide your final response NOW. No more tool calls unless absolutely critical.]"},
+        ]
+        _strip_budget_warnings_from_history(messages)
+        assert messages[0]["content"] == "some result"
+
+    def test_leaves_non_tool_messages_unchanged(self):
+        from run_agent import _strip_budget_warnings_from_history
+
+        messages = [
+            {"role": "assistant", "content": "[BUDGET WARNING: Iteration 58/60. Only 2 iteration(s) left. Provide your final response NOW. No more tool calls unless absolutely critical.]"},
+            {"role": "user", "content": "hello"},
+        ]
+        original_contents = [m["content"] for m in messages]
+        _strip_budget_warnings_from_history(messages)
+        assert [m["content"] for m in messages] == original_contents
+
+    def test_handles_empty_and_missing_content(self):
+        from run_agent import _strip_budget_warnings_from_history
+
+        messages = [
+            {"role": "tool", "tool_call_id": "c1", "content": ""},
+            {"role": "tool", "tool_call_id": "c2"},
+        ]
+        _strip_budget_warnings_from_history(messages)
+        assert messages[0]["content"] == ""
+
+    def test_strips_caution_variant(self):
+        import json
+        from run_agent import _strip_budget_warnings_from_history
+
+        messages = [
+            {"role": "tool", "tool_call_id": "c1", "content": json.dumps({
+                "output": "ok",
+                "_budget_warning": "[BUDGET: Iteration 42/60. 18 iterations left. Start consolidating your work.]",
+            })},
+        ]
+        _strip_budget_warnings_from_history(messages)
+        parsed = json.loads(messages[0]["content"])
+        assert "_budget_warning" not in parsed
@@ -54,7 +54,7 @@ class TestScanSkillCommands:
        """macOS-only skills should not register slash commands on Linux."""
        with (
            patch("tools.skills_tool.SKILLS_DIR", tmp_path),
-            patch("tools.skills_tool.sys") as mock_sys,
+            patch("agent.skill_utils.sys") as mock_sys,
        ):
            mock_sys.platform = "linux"
            _make_skill(tmp_path, "imessage", frontmatter_extra="platforms: [macos]\n")
@@ -67,7 +67,7 @@ class TestScanSkillCommands:
        """macOS-only skills should register slash commands on macOS."""
        with (
            patch("tools.skills_tool.SKILLS_DIR", tmp_path),
-            patch("tools.skills_tool.sys") as mock_sys,
+            patch("agent.skill_utils.sys") as mock_sys,
        ):
            mock_sys.platform = "darwin"
            _make_skill(tmp_path, "imessage", frontmatter_extra="platforms: [macos]\n")
@@ -78,7 +78,7 @@ class TestScanSkillCommands:
        """Skills without platforms field should register on any platform."""
        with (
            patch("tools.skills_tool.SKILLS_DIR", tmp_path),
-            patch("tools.skills_tool.sys") as mock_sys,
+            patch("agent.skill_utils.sys") as mock_sys,
        ):
            mock_sys.platform = "win32"
            _make_skill(tmp_path, "generic-tool")
@@ -20,6 +20,7 @@ from cron.jobs import (
    resume_job,
    remove_job,
    mark_job_run,
+    advance_next_run,
    get_due_jobs,
    save_job_output,
 )
@@ -339,6 +340,90 @@ class TestMarkJobRun:
        assert updated["last_error"] == "timeout"


+class TestAdvanceNextRun:
+    """Tests for advance_next_run() — crash-safety for recurring jobs."""
+
+    def test_advances_interval_job(self, tmp_cron_dir):
+        """Interval jobs should have next_run_at bumped to the next future occurrence."""
+        job = create_job(prompt="Recurring check", schedule="every 1h")
+        # Force next_run_at to 5 minutes ago (i.e. the job is due)
+        jobs = load_jobs()
+        old_next = (datetime.now() - timedelta(minutes=5)).isoformat()
+        jobs[0]["next_run_at"] = old_next
+        save_jobs(jobs)
+
+        result = advance_next_run(job["id"])
+        assert result is True
+
+        updated = get_job(job["id"])
+        from cron.jobs import _ensure_aware, _hermes_now
+        new_next_dt = _ensure_aware(datetime.fromisoformat(updated["next_run_at"]))
+        assert new_next_dt > _hermes_now(), "next_run_at should be in the future after advance"
+
+    def test_advances_cron_job(self, tmp_cron_dir):
+        """Cron-expression jobs should have next_run_at bumped to the next occurrence."""
+        pytest.importorskip("croniter")
+        job = create_job(prompt="Daily wakeup", schedule="15 6 * * *")
+        # Force next_run_at to 30 minutes ago
+        jobs = load_jobs()
+        old_next = (datetime.now() - timedelta(minutes=30)).isoformat()
+        jobs[0]["next_run_at"] = old_next
+        save_jobs(jobs)
+
+        result = advance_next_run(job["id"])
+        assert result is True
+
+        updated = get_job(job["id"])
+        from cron.jobs import _ensure_aware, _hermes_now
+        new_next_dt = _ensure_aware(datetime.fromisoformat(updated["next_run_at"]))
+        assert new_next_dt > _hermes_now(), "next_run_at should be in the future after advance"
+
+    def test_skips_oneshot_job(self, tmp_cron_dir):
+        """One-shot jobs should NOT be advanced — they need to retry on restart."""
+        job = create_job(prompt="Run once", schedule="30m")
+        original_next = get_job(job["id"])["next_run_at"]
+
+        result = advance_next_run(job["id"])
+        assert result is False
+
+        updated = get_job(job["id"])
+        assert updated["next_run_at"] == original_next, "one-shot next_run_at should be unchanged"
+
+    def test_nonexistent_job_returns_false(self, tmp_cron_dir):
+        result = advance_next_run("nonexistent-id")
+        assert result is False
+
+    def test_already_future_stays_future(self, tmp_cron_dir):
+        """If next_run_at is already in the future, advance keeps it in the future (no harm)."""
+        job = create_job(prompt="Future job", schedule="every 1h")
+        # next_run_at is already set to ~1h from now by create_job
+        advance_next_run(job["id"])
+        # Regardless of return value, the job should still be in the future
+        updated = get_job(job["id"])
+        from cron.jobs import _ensure_aware, _hermes_now
+        new_next_dt = _ensure_aware(datetime.fromisoformat(updated["next_run_at"]))
+        assert new_next_dt > _hermes_now(), "next_run_at should remain in the future"
+
+    def test_crash_safety_scenario(self, tmp_cron_dir):
+        """Simulate the crash-loop scenario: after advance, the job should NOT be due."""
+        job = create_job(prompt="Crash test", schedule="every 1h")
+        # Force next_run_at to 5 minutes ago (job is due)
+        jobs = load_jobs()
+        jobs[0]["next_run_at"] = (datetime.now() - timedelta(minutes=5)).isoformat()
+        save_jobs(jobs)
+
+        # Job should be due before advance
+        due_before = get_due_jobs()
+        assert len(due_before) == 1
+
+        # Advance (simulating what tick() does before run_job)
+        advance_next_run(job["id"])
+
+        # Now the job should NOT be due (simulates restart after crash)
+        due_after = get_due_jobs()
+        assert len(due_after) == 0, "Job should not be due after advance_next_run"
+
+
 class TestGetDueJobs:
    def test_past_due_within_window_returned(self, tmp_cron_dir):
        """Jobs within the dynamic grace window are still considered due (not stale).
@@ -687,3 +687,41 @@ class TestBuildJobPromptMissingSkill:
            result = _build_job_prompt({"skills": ["ghost-skill", "real-skill"], "prompt": "go"})
        assert "Real skill content." in result
        assert "go" in result
+
+
+class TestTickAdvanceBeforeRun:
+    """Verify that tick() calls advance_next_run before run_job for crash safety."""
+
+    def test_advance_called_before_run_job(self, tmp_path):
+        """advance_next_run must be called before run_job to prevent crash-loop re-fires."""
+        call_order = []
+
+        def fake_advance(job_id):
+            call_order.append(("advance", job_id))
+            return True
+
+        def fake_run_job(job):
+            call_order.append(("run", job["id"]))
+            return True, "output", "response", None
+
+        fake_job = {
+            "id": "test-advance",
+            "name": "test",
+            "prompt": "hello",
+            "enabled": True,
+            "schedule": {"kind": "cron", "expr": "15 6 * * *"},
+        }
+
+        with patch("cron.scheduler.get_due_jobs", return_value=[fake_job]), \
+             patch("cron.scheduler.advance_next_run", side_effect=fake_advance) as adv_mock, \
+             patch("cron.scheduler.run_job", side_effect=fake_run_job), \
+             patch("cron.scheduler.save_job_output", return_value=tmp_path / "out.md"), \
+             patch("cron.scheduler.mark_job_run"), \
+             patch("cron.scheduler._deliver_result"):
+            from cron.scheduler import tick
+            executed = tick(verbose=False)
+
+        assert executed == 1
+        adv_mock.assert_called_once_with("test-advance")
+        # advance must happen before run
+        assert call_order == [("advance", "test-advance"), ("run", "test-advance")]
@@ -0,0 +1,46 @@
+"""Tests for the startup allowlist warning check in gateway/run.py."""
+
+import os
+from unittest.mock import patch
+
+
+def _would_warn():
+    """Replicate the startup allowlist warning logic. Returns True if warning fires."""
+    _any_allowlist = any(
+        os.getenv(v)
+        for v in ("TELEGRAM_ALLOWED_USERS", "DISCORD_ALLOWED_USERS",
+                   "WHATSAPP_ALLOWED_USERS", "SLACK_ALLOWED_USERS",
+                   "SIGNAL_ALLOWED_USERS", "SIGNAL_GROUP_ALLOWED_USERS",
+                   "EMAIL_ALLOWED_USERS",
+                   "SMS_ALLOWED_USERS", "MATTERMOST_ALLOWED_USERS",
+                   "MATRIX_ALLOWED_USERS", "DINGTALK_ALLOWED_USERS",
+                   "GATEWAY_ALLOWED_USERS")
+    )
+    _allow_all = os.getenv("GATEWAY_ALLOW_ALL_USERS", "").lower() in ("true", "1", "yes") or any(
+        os.getenv(v, "").lower() in ("true", "1", "yes")
+        for v in ("TELEGRAM_ALLOW_ALL_USERS", "DISCORD_ALLOW_ALL_USERS",
+                   "WHATSAPP_ALLOW_ALL_USERS", "SLACK_ALLOW_ALL_USERS",
+                   "SIGNAL_ALLOW_ALL_USERS", "EMAIL_ALLOW_ALL_USERS",
+                   "SMS_ALLOW_ALL_USERS", "MATTERMOST_ALLOW_ALL_USERS",
+                   "MATRIX_ALLOW_ALL_USERS", "DINGTALK_ALLOW_ALL_USERS")
+    )
+    return not _any_allowlist and not _allow_all
+
+
+class TestAllowlistStartupCheck:
+
+    def test_no_config_emits_warning(self):
+        with patch.dict(os.environ, {}, clear=True):
+            assert _would_warn() is True
+
+    def test_signal_group_allowed_users_suppresses_warning(self):
+        with patch.dict(os.environ, {"SIGNAL_GROUP_ALLOWED_USERS": "user1"}, clear=True):
+            assert _would_warn() is False
+
+    def test_telegram_allow_all_users_suppresses_warning(self):
+        with patch.dict(os.environ, {"TELEGRAM_ALLOW_ALL_USERS": "true"}, clear=True):
+            assert _would_warn() is False
+
+    def test_gateway_allow_all_users_suppresses_warning(self):
+        with patch.dict(os.environ, {"GATEWAY_ALLOW_ALL_USERS": "yes"}, clear=True):
+            assert _would_warn() is False
@@ -28,6 +28,7 @@ from gateway.platforms.api_server import (
    _CORS_HEADERS,
    check_api_server_requirements,
    cors_middleware,
+    security_headers_middleware,
 )


@@ -214,9 +215,11 @@ def _make_adapter(api_key: str = "", cors_origins=None) -> APIServerAdapter:

 def _create_app(adapter: APIServerAdapter) -> web.Application:
    """Create the aiohttp app from the adapter (without starting the full server)."""
-    app = web.Application(middlewares=[cors_middleware])
+    mws = [mw for mw in (cors_middleware, security_headers_middleware) if mw is not None]
+    app = web.Application(middlewares=mws)
    app["api_server_adapter"] = adapter
    app.router.add_get("/health", adapter._handle_health)
+    app.router.add_get("/v1/health", adapter._handle_health)
    app.router.add_get("/v1/models", adapter._handle_models)
    app.router.add_post("/v1/chat/completions", adapter._handle_chat_completions)
    app.router.add_post("/v1/responses", adapter._handle_responses)
@@ -241,6 +244,16 @@ def auth_adapter():


 class TestHealthEndpoint:
+    @pytest.mark.asyncio
+    async def test_security_headers_present(self, adapter):
+        """Responses should include basic security headers."""
+        app = _create_app(adapter)
+        async with TestClient(TestServer(app)) as cli:
+            resp = await cli.get("/health")
+            assert resp.status == 200
+            assert resp.headers.get("X-Content-Type-Options") == "nosniff"
+            assert resp.headers.get("Referrer-Policy") == "no-referrer"
+
    @pytest.mark.asyncio
    async def test_health_returns_ok(self, adapter):
        app = _create_app(adapter)
@@ -251,6 +264,17 @@ class TestHealthEndpoint:
            assert data["status"] == "ok"
            assert data["platform"] == "hermes-agent"

+    @pytest.mark.asyncio
+    async def test_v1_health_alias_returns_ok(self, adapter):
+        """GET /v1/health should return the same response as /health."""
+        app = _create_app(adapter)
+        async with TestClient(TestServer(app)) as cli:
+            resp = await cli.get("/v1/health")
+            assert resp.status == 200
+            data = await resp.json()
+            assert data["status"] == "ok"
+            assert data["platform"] == "hermes-agent"
+

 # ---------------------------------------------------------------------------
 # /v1/models endpoint
@@ -1300,6 +1324,31 @@ class TestCORS:
            assert "POST" in resp.headers.get("Access-Control-Allow-Methods", "")
            assert "DELETE" in resp.headers.get("Access-Control-Allow-Methods", "")

+    @pytest.mark.asyncio
+    async def test_cors_allows_idempotency_key_header(self):
+        adapter = _make_adapter(cors_origins=["http://localhost:3000"])
+        app = _create_app(adapter)
+        async with TestClient(TestServer(app)) as cli:
+            resp = await cli.options(
+                "/v1/chat/completions",
+                headers={
+                    "Origin": "http://localhost:3000",
+                    "Access-Control-Request-Method": "POST",
+                    "Access-Control-Request-Headers": "Idempotency-Key",
+                },
+            )
+            assert resp.status == 200
+            assert "Idempotency-Key" in resp.headers.get("Access-Control-Allow-Headers", "")
+
+    @pytest.mark.asyncio
+    async def test_cors_sets_vary_origin_header(self):
+        adapter = _make_adapter(cors_origins=["http://localhost:3000"])
+        app = _create_app(adapter)
+        async with TestClient(TestServer(app)) as cli:
+            resp = await cli.get("/health", headers={"Origin": "http://localhost:3000"})
+            assert resp.status == 200
+            assert resp.headers.get("Vary") == "Origin"
+
    @pytest.mark.asyncio
    async def test_cors_options_preflight_allowed_for_configured_origin(self):
        """Configured origins can complete browser preflight."""
@@ -1319,6 +1368,21 @@ class TestCORS:
            assert "Authorization" in resp.headers.get("Access-Control-Allow-Headers", "")


+    @pytest.mark.asyncio
+    async def test_cors_preflight_sets_max_age(self):
+        adapter = _make_adapter(cors_origins=["http://localhost:3000"])
+        app = _create_app(adapter)
+        async with TestClient(TestServer(app)) as cli:
+            resp = await cli.options(
+                "/v1/chat/completions",
+                headers={
+                    "Origin": "http://localhost:3000",
+                    "Access-Control-Request-Method": "POST",
+                    "Access-Control-Request-Headers": "Authorization, Content-Type",
+                },
+            )
+            assert resp.status == 200
+            assert resp.headers.get("Access-Control-Max-Age") == "600"
 # ---------------------------------------------------------------------------
 # Conversation parameter
 # ---------------------------------------------------------------------------
@@ -69,7 +69,8 @@ class TestApiServerPlatformConfig:

 class TestApiServerAdapterToolset:
    @patch("gateway.platforms.api_server.AIOHTTP_AVAILABLE", True)
-    def test_create_agent_uses_api_server_toolset(self):
+    def test_create_agent_reads_config_toolsets(self):
+        """API server resolves toolsets from config like all other platforms."""
        from gateway.platforms.api_server import APIServerAdapter
        from gateway.config import PlatformConfig

@@ -77,17 +78,52 @@ class TestApiServerAdapterToolset:

        with patch("gateway.run._resolve_runtime_agent_kwargs") as mock_kwargs, \
             patch("gateway.run._resolve_gateway_model") as mock_model, \
+             patch("gateway.run._load_gateway_config") as mock_config, \
             patch("run_agent.AIAgent") as mock_agent_cls:

            mock_kwargs.return_value = {"api_key": "test-key", "base_url": None,
                                        "provider": None, "api_mode": None,
                                        "command": None, "args": []}
            mock_model.return_value = "test/model"
+            # No platform_toolsets override — should fall back to hermes-api-server default
+            mock_config.return_value = {}
            mock_agent_cls.return_value = MagicMock()

            adapter._create_agent()

            mock_agent_cls.assert_called_once()
            call_kwargs = mock_agent_cls.call_args
-            assert call_kwargs.kwargs.get("enabled_toolsets") == ["hermes-api-server"]
+            toolsets = call_kwargs.kwargs.get("enabled_toolsets")
+            assert isinstance(toolsets, list)
+            assert len(toolsets) > 0
            assert call_kwargs.kwargs.get("platform") == "api_server"
+
+    @patch("gateway.platforms.api_server.AIOHTTP_AVAILABLE", True)
+    def test_create_agent_respects_config_override(self):
+        """User can override API server toolsets via platform_toolsets in config.yaml."""
+        from gateway.platforms.api_server import APIServerAdapter
+        from gateway.config import PlatformConfig
+
+        adapter = APIServerAdapter(PlatformConfig())
+
+        with patch("gateway.run._resolve_runtime_agent_kwargs") as mock_kwargs, \
+             patch("gateway.run._resolve_gateway_model") as mock_model, \
+             patch("gateway.run._load_gateway_config") as mock_config, \
+             patch("run_agent.AIAgent") as mock_agent_cls:
+
+            mock_kwargs.return_value = {"api_key": "test-key", "base_url": None,
+                                        "provider": None, "api_mode": None,
+                                        "command": None, "args": []}
+            mock_model.return_value = "test/model"
+            # User overrides with just web and terminal
+            mock_config.return_value = {
+                "platform_toolsets": {"api_server": ["web", "terminal"]}
+            }
+            mock_agent_cls.return_value = MagicMock()
+
+            adapter._create_agent()
+
+            mock_agent_cls.assert_called_once()
+            call_kwargs = mock_agent_cls.call_args
+            toolsets = call_kwargs.kwargs.get("enabled_toolsets")
+            assert sorted(toolsets) == ["terminal", "web"]
@@ -10,6 +10,7 @@ Covers:
 """

 import asyncio
+import os
 import sys
 from pathlib import Path
 from types import SimpleNamespace
@@ -32,7 +33,7 @@ def _ensure_telegram_mock():
    telegram_mod.constants.ChatType.CHANNEL = "channel"
    telegram_mod.constants.ChatType.PRIVATE = "private"

-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, telegram_mod)


@@ -227,7 +228,8 @@ def test_persist_dm_topic_thread_id_writes_config(tmp_path):

    adapter = _make_adapter()

-    with patch.object(Path, "home", return_value=tmp_path):
+    with patch.object(Path, "home", return_value=tmp_path), \
+         patch.dict(os.environ, {"HERMES_HOME": str(tmp_path / ".hermes")}):
        adapter._persist_dm_topic_thread_id(111, "General", 999)

    with open(config_file) as f:
@@ -366,7 +368,8 @@ def test_get_dm_topic_info_hot_reloads_from_config(tmp_path):
    with open(config_file, "w") as f:
        yaml.dump(config_data, f)

-    with patch.object(Path, "home", return_value=tmp_path):
+    with patch.object(Path, "home", return_value=tmp_path), \
+         patch.dict(os.environ, {"HERMES_HOME": str(tmp_path / ".hermes")}):
        result = adapter._get_dm_topic_info("111", "555")

    assert result is not None
@@ -7,11 +7,21 @@ Verifies that:
 3. The flush still works normally when memory files don't exist
 """

+import sys
+import types
 import pytest
 from pathlib import Path
 from unittest.mock import MagicMock, patch, call


+@pytest.fixture(autouse=True)
+def _mock_dotenv(monkeypatch):
+    """gateway.run imports dotenv at module level; stub it so tests run without the package."""
+    fake = types.ModuleType("dotenv")
+    fake.load_dotenv = lambda *a, **kw: None
+    monkeypatch.setitem(sys.modules, "dotenv", fake)
+
+
 def _make_runner():
    from gateway.run import GatewayRunner

@@ -57,105 +67,151 @@ class TestCronSessionBypass:
        runner.session_store.load_transcript.assert_called_once_with("session_abc123")


+def _make_flush_context(monkeypatch, memory_dir=None):
+    """Return (runner, tmp_agent, fake_run_agent) with run_agent mocked in sys.modules."""
+    tmp_agent = MagicMock()
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = MagicMock(return_value=tmp_agent)
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    runner = _make_runner()
+    runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
+    return runner, tmp_agent, memory_dir
+
+
 class TestMemoryInjection:
    """The flush prompt should include current memory state from disk."""

-    def test_memory_content_injected_into_flush_prompt(self, tmp_path):
+    def test_memory_content_injected_into_flush_prompt(self, tmp_path, monkeypatch):
        """When memory files exist, their content appears in the flush prompt."""
-        runner = _make_runner()
-        runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
-
-        tmp_agent = MagicMock()
        memory_dir = tmp_path / "memories"
        memory_dir.mkdir()
        (memory_dir / "MEMORY.md").write_text("Agent knows Python\n§\nUser prefers dark mode")
        (memory_dir / "USER.md").write_text("Name: Alice\n§\nTimezone: PST")

+        runner, tmp_agent, _ = _make_flush_context(monkeypatch, memory_dir)
+
        with (
            patch("gateway.run._resolve_runtime_agent_kwargs", return_value={"api_key": "k"}),
            patch("gateway.run._resolve_gateway_model", return_value="test-model"),
-            patch("run_agent.AIAgent", return_value=tmp_agent),
-            # Intercept `from tools.memory_tool import MEMORY_DIR` inside the function
            patch.dict("sys.modules", {"tools.memory_tool": MagicMock(MEMORY_DIR=memory_dir)}),
        ):
            runner._flush_memories_for_session("session_123")

        tmp_agent.run_conversation.assert_called_once()
-        call_kwargs = tmp_agent.run_conversation.call_args.kwargs
-        flush_prompt = call_kwargs.get("user_message", "")
-        
-        # Verify both memory sections appear in the prompt
+        flush_prompt = tmp_agent.run_conversation.call_args.kwargs.get("user_message", "")
+
        assert "Agent knows Python" in flush_prompt
        assert "User prefers dark mode" in flush_prompt
        assert "Name: Alice" in flush_prompt
        assert "Timezone: PST" in flush_prompt
-        # Verify the stale-overwrite warning is present
        assert "Do NOT overwrite or remove entries" in flush_prompt
        assert "current live state of memory" in flush_prompt

-    def test_flush_works_without_memory_files(self, tmp_path):
+    def test_flush_works_without_memory_files(self, tmp_path, monkeypatch):
        """When no memory files exist, flush still runs without the guard."""
-        runner = _make_runner()
-        runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
-
-        tmp_agent = MagicMock()
        empty_dir = tmp_path / "no_memories"
        empty_dir.mkdir()

+        runner, tmp_agent, _ = _make_flush_context(monkeypatch)
+
        with (
            patch("gateway.run._resolve_runtime_agent_kwargs", return_value={"api_key": "k"}),
            patch("gateway.run._resolve_gateway_model", return_value="test-model"),
-            patch("run_agent.AIAgent", return_value=tmp_agent),
            patch.dict("sys.modules", {"tools.memory_tool": MagicMock(MEMORY_DIR=empty_dir)}),
        ):
            runner._flush_memories_for_session("session_456")

-        # Should still run, just without the memory guard section
        tmp_agent.run_conversation.assert_called_once()
        flush_prompt = tmp_agent.run_conversation.call_args.kwargs.get("user_message", "")
        assert "Do NOT overwrite or remove entries" not in flush_prompt
        assert "Review the conversation above" in flush_prompt

-    def test_empty_memory_files_no_injection(self, tmp_path):
+    def test_empty_memory_files_no_injection(self, tmp_path, monkeypatch):
        """Empty memory files should not trigger the guard section."""
-        runner = _make_runner()
-        runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
-
-        tmp_agent = MagicMock()
        memory_dir = tmp_path / "memories"
        memory_dir.mkdir()
        (memory_dir / "MEMORY.md").write_text("")
        (memory_dir / "USER.md").write_text("  \n  ")  # whitespace only

+        runner, tmp_agent, _ = _make_flush_context(monkeypatch)
+
        with (
            patch("gateway.run._resolve_runtime_agent_kwargs", return_value={"api_key": "k"}),
            patch("gateway.run._resolve_gateway_model", return_value="test-model"),
-            patch("run_agent.AIAgent", return_value=tmp_agent),
            patch.dict("sys.modules", {"tools.memory_tool": MagicMock(MEMORY_DIR=memory_dir)}),
        ):
            runner._flush_memories_for_session("session_789")

        tmp_agent.run_conversation.assert_called_once()
        flush_prompt = tmp_agent.run_conversation.call_args.kwargs.get("user_message", "")
-        # No memory content → no guard section
        assert "current live state of memory" not in flush_prompt


+class TestFlushAgentSilenced:
+    """The flush agent must not produce any terminal output."""
+
+    def test_print_fn_set_to_noop(self, tmp_path, monkeypatch):
+        """_print_fn on the flush agent must be a no-op so tool output never leaks."""
+        runner = _make_runner()
+        runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
+
+        captured_agent = {}
+
+        def _fake_ai_agent(*args, **kwargs):
+            agent = MagicMock()
+            captured_agent["instance"] = agent
+            return agent
+
+        fake_run_agent = types.ModuleType("run_agent")
+        fake_run_agent.AIAgent = _fake_ai_agent
+        monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+        with (
+            patch("gateway.run._resolve_runtime_agent_kwargs", return_value={"api_key": "k"}),
+            patch("gateway.run._resolve_gateway_model", return_value="test-model"),
+            patch.dict("sys.modules", {"tools.memory_tool": MagicMock(MEMORY_DIR=tmp_path)}),
+        ):
+            runner._flush_memories_for_session("session_silent")
+
+        agent = captured_agent["instance"]
+        assert agent._print_fn is not None, "_print_fn should be overridden to suppress output"
+        # Confirm it is callable and produces no output (no exception)
+        agent._print_fn("should be silenced")
+
+    def test_kawaii_spinner_respects_print_fn(self):
+        """KawaiiSpinner must route all output through print_fn when supplied."""
+        from agent.display import KawaiiSpinner
+
+        written = []
+        spinner = KawaiiSpinner("test", print_fn=lambda *a, **kw: written.append(a))
+        spinner._write("hello")
+        assert written == [("hello",)], "spinner should route through print_fn"
+
+        # A no-op print_fn must produce no output to stdout
+        import io, sys
+        buf = io.StringIO()
+        old_stdout = sys.stdout
+        sys.stdout = buf
+        try:
+            silent_spinner = KawaiiSpinner("silent", print_fn=lambda *a, **kw: None)
+            silent_spinner._write("should not appear")
+            silent_spinner.stop("done")
+        finally:
+            sys.stdout = old_stdout
+        assert buf.getvalue() == "", "no-op print_fn spinner must not write to stdout"
+
+
 class TestFlushPromptStructure:
    """Verify the flush prompt retains its core instructions."""

-    def test_core_instructions_present(self):
+    def test_core_instructions_present(self, monkeypatch):
        """The flush prompt should still contain the original guidance."""
-        runner = _make_runner()
-        runner.session_store.load_transcript.return_value = _TRANSCRIPT_4_MSGS
-
-        tmp_agent = MagicMock()
+        runner, tmp_agent, _ = _make_flush_context(monkeypatch)

        with (
            patch("gateway.run._resolve_runtime_agent_kwargs", return_value={"api_key": "k"}),
            patch("gateway.run._resolve_gateway_model", return_value="test-model"),
-            patch("run_agent.AIAgent", return_value=tmp_agent),
-            # Make the import fail gracefully so we test without memory files
            patch.dict("sys.modules", {"tools.memory_tool": MagicMock(MEMORY_DIR=Path("/nonexistent"))}),
        ):
            runner._flush_memories_for_session("session_struct")
@@ -1,4 +1,5 @@
 """Tests for Matrix platform adapter."""
+import asyncio
 import json
 import re
 import pytest
@@ -446,3 +447,199 @@ class TestMatrixRequirements:
        monkeypatch.delenv("MATRIX_HOMESERVER", raising=False)
        from gateway.platforms.matrix import check_matrix_requirements
        assert check_matrix_requirements() is False
+
+
+# ---------------------------------------------------------------------------
+# Access-token auth / E2EE bootstrap
+# ---------------------------------------------------------------------------
+
+class TestMatrixAccessTokenAuth:
+    @pytest.mark.asyncio
+    async def test_connect_fetches_device_id_from_whoami_for_access_token(self):
+        from gateway.platforms.matrix import MatrixAdapter
+
+        config = PlatformConfig(
+            enabled=True,
+            token="syt_test_access_token",
+            extra={
+                "homeserver": "https://matrix.example.org",
+                "user_id": "@bot:example.org",
+                "encryption": True,
+            },
+        )
+        adapter = MatrixAdapter(config)
+
+        class FakeWhoamiResponse:
+            def __init__(self, user_id, device_id):
+                self.user_id = user_id
+                self.device_id = device_id
+
+        class FakeSyncResponse:
+            def __init__(self):
+                self.rooms = MagicMock(join={})
+
+        fake_client = MagicMock()
+        fake_client.whoami = AsyncMock(return_value=FakeWhoamiResponse("@bot:example.org", "DEV123"))
+        fake_client.sync = AsyncMock(return_value=FakeSyncResponse())
+        fake_client.keys_upload = AsyncMock()
+        fake_client.keys_query = AsyncMock()
+        fake_client.keys_claim = AsyncMock()
+        fake_client.send_to_device_messages = AsyncMock(return_value=[])
+        fake_client.get_users_for_key_claiming = MagicMock(return_value={})
+        fake_client.close = AsyncMock()
+        fake_client.add_event_callback = MagicMock()
+        fake_client.rooms = {}
+        fake_client.account_data = {}
+        fake_client.olm = object()
+        fake_client.should_upload_keys = False
+        fake_client.should_query_keys = False
+        fake_client.should_claim_keys = False
+
+        def _restore_login(user_id, device_id, access_token):
+            fake_client.user_id = user_id
+            fake_client.device_id = device_id
+            fake_client.access_token = access_token
+            fake_client.olm = object()
+
+        fake_client.restore_login = MagicMock(side_effect=_restore_login)
+
+        fake_nio = MagicMock()
+        fake_nio.AsyncClient = MagicMock(return_value=fake_client)
+        fake_nio.WhoamiResponse = FakeWhoamiResponse
+        fake_nio.SyncResponse = FakeSyncResponse
+        fake_nio.LoginResponse = type("LoginResponse", (), {})
+        fake_nio.RoomMessageText = type("RoomMessageText", (), {})
+        fake_nio.RoomMessageImage = type("RoomMessageImage", (), {})
+        fake_nio.RoomMessageAudio = type("RoomMessageAudio", (), {})
+        fake_nio.RoomMessageVideo = type("RoomMessageVideo", (), {})
+        fake_nio.RoomMessageFile = type("RoomMessageFile", (), {})
+        fake_nio.InviteMemberEvent = type("InviteMemberEvent", (), {})
+        fake_nio.MegolmEvent = type("MegolmEvent", (), {})
+
+        with patch.dict("sys.modules", {"nio": fake_nio}):
+            with patch.object(adapter, "_refresh_dm_cache", AsyncMock()):
+                with patch.object(adapter, "_sync_loop", AsyncMock(return_value=None)):
+                    assert await adapter.connect() is True
+
+        fake_client.restore_login.assert_called_once_with(
+            "@bot:example.org", "DEV123", "syt_test_access_token"
+        )
+        assert fake_client.access_token == "syt_test_access_token"
+        assert fake_client.user_id == "@bot:example.org"
+        assert fake_client.device_id == "DEV123"
+        fake_client.whoami.assert_awaited_once()
+
+        await adapter.disconnect()
+
+
+class TestMatrixE2EEMaintenance:
+    @pytest.mark.asyncio
+    async def test_sync_loop_runs_e2ee_maintenance_requests(self):
+        adapter = _make_adapter()
+        adapter._encryption = True
+        adapter._closing = False
+
+        class FakeSyncError:
+            pass
+
+        async def _sync_once(timeout=30000):
+            adapter._closing = True
+            return MagicMock()
+
+        fake_client = MagicMock()
+        fake_client.sync = AsyncMock(side_effect=_sync_once)
+        fake_client.send_to_device_messages = AsyncMock(return_value=[])
+        fake_client.keys_upload = AsyncMock()
+        fake_client.keys_query = AsyncMock()
+        fake_client.get_users_for_key_claiming = MagicMock(
+            return_value={"@alice:example.org": ["DEVICE1"]}
+        )
+        fake_client.keys_claim = AsyncMock()
+        fake_client.olm = object()
+        fake_client.should_upload_keys = True
+        fake_client.should_query_keys = True
+        fake_client.should_claim_keys = True
+
+        adapter._client = fake_client
+
+        fake_nio = MagicMock()
+        fake_nio.SyncError = FakeSyncError
+
+        with patch.dict("sys.modules", {"nio": fake_nio}):
+            await adapter._sync_loop()
+
+        fake_client.sync.assert_awaited_once_with(timeout=30000)
+        fake_client.send_to_device_messages.assert_awaited_once()
+        fake_client.keys_upload.assert_awaited_once()
+        fake_client.keys_query.assert_awaited_once()
+        fake_client.keys_claim.assert_awaited_once_with(
+            {"@alice:example.org": ["DEVICE1"]}
+        )
+
+
+class TestMatrixEncryptedSendFallback:
+    @pytest.mark.asyncio
+    async def test_send_retries_with_ignored_unverified_devices(self):
+        adapter = _make_adapter()
+        adapter._encryption = True
+
+        class FakeRoomSendResponse:
+            def __init__(self, event_id):
+                self.event_id = event_id
+
+        class FakeOlmUnverifiedDeviceError(Exception):
+            pass
+
+        fake_client = MagicMock()
+        fake_client.room_send = AsyncMock(side_effect=[
+            FakeOlmUnverifiedDeviceError("unverified"),
+            FakeRoomSendResponse("$event123"),
+        ])
+        adapter._client = fake_client
+        adapter._run_e2ee_maintenance = AsyncMock()
+
+        fake_nio = MagicMock()
+        fake_nio.RoomSendResponse = FakeRoomSendResponse
+        fake_nio.OlmUnverifiedDeviceError = FakeOlmUnverifiedDeviceError
+
+        with patch.dict("sys.modules", {"nio": fake_nio}):
+            result = await adapter.send("!room:example.org", "hello")
+
+        assert result.success is True
+        assert result.message_id == "$event123"
+        adapter._run_e2ee_maintenance.assert_awaited_once()
+        assert fake_client.room_send.await_count == 2
+        first_call = fake_client.room_send.await_args_list[0]
+        second_call = fake_client.room_send.await_args_list[1]
+        assert first_call.kwargs.get("ignore_unverified_devices") is False
+        assert second_call.kwargs.get("ignore_unverified_devices") is True
+
+    @pytest.mark.asyncio
+    async def test_send_retries_after_timeout_in_encrypted_room(self):
+        adapter = _make_adapter()
+        adapter._encryption = True
+
+        class FakeRoomSendResponse:
+            def __init__(self, event_id):
+                self.event_id = event_id
+
+        fake_client = MagicMock()
+        fake_client.room_send = AsyncMock(side_effect=[
+            asyncio.TimeoutError(),
+            FakeRoomSendResponse("$event456"),
+        ])
+        adapter._client = fake_client
+        adapter._run_e2ee_maintenance = AsyncMock()
+
+        fake_nio = MagicMock()
+        fake_nio.RoomSendResponse = FakeRoomSendResponse
+
+        with patch.dict("sys.modules", {"nio": fake_nio}):
+            result = await adapter.send("!room:example.org", "hello")
+
+        assert result.success is True
+        assert result.message_id == "$event456"
+        adapter._run_e2ee_maintenance.assert_awaited_once()
+        assert fake_client.room_send.await_count == 2
+        second_call = fake_client.room_send.await_args_list[1]
+        assert second_call.kwargs.get("ignore_unverified_devices") is True
@@ -1,5 +1,6 @@
 """Tests for Mattermost platform adapter."""
 import json
+import os
 import time
 import pytest
 from unittest.mock import MagicMock, patch, AsyncMock
@@ -269,6 +270,7 @@ class TestMattermostWebSocketParsing:
    def setup_method(self):
        self.adapter = _make_adapter()
        self.adapter._bot_user_id = "bot_user_id"
+        self.adapter._bot_username = "hermes-bot"
        # Mock handle_message to capture the MessageEvent without processing
        self.adapter.handle_message = AsyncMock()

@@ -293,7 +295,8 @@ class TestMattermostWebSocketParsing:
        await self.adapter._handle_ws_event(event)
        assert self.adapter.handle_message.called
        msg_event = self.adapter.handle_message.call_args[0][0]
-        assert msg_event.text == "@bot_user_id Hello from Matrix!"
+        # @mention is stripped from the message text
+        assert msg_event.text == "Hello from Matrix!"
        assert msg_event.message_id == "post_abc"

    @pytest.mark.asyncio
@@ -410,6 +413,87 @@ class TestMattermostWebSocketParsing:
        assert not self.adapter.handle_message.called


+# ---------------------------------------------------------------------------
+# Mention behavior (require_mention + free_response_channels)
+# ---------------------------------------------------------------------------
+
+class TestMattermostMentionBehavior:
+    def setup_method(self):
+        self.adapter = _make_adapter()
+        self.adapter._bot_user_id = "bot_user_id"
+        self.adapter._bot_username = "hermes-bot"
+        self.adapter.handle_message = AsyncMock()
+
+    def _make_event(self, message, channel_type="O", channel_id="chan_456"):
+        post_data = {
+            "id": "post_mention",
+            "user_id": "user_123",
+            "channel_id": channel_id,
+            "message": message,
+        }
+        return {
+            "event": "posted",
+            "data": {
+                "post": json.dumps(post_data),
+                "channel_type": channel_type,
+                "sender_name": "@alice",
+            },
+        }
+
+    @pytest.mark.asyncio
+    async def test_require_mention_true_skips_without_mention(self):
+        """Default: messages without @mention in channels are skipped."""
+        with patch.dict(os.environ, {}, clear=False):
+            os.environ.pop("MATTERMOST_REQUIRE_MENTION", None)
+            os.environ.pop("MATTERMOST_FREE_RESPONSE_CHANNELS", None)
+            await self.adapter._handle_ws_event(self._make_event("hello"))
+            assert not self.adapter.handle_message.called
+
+    @pytest.mark.asyncio
+    async def test_require_mention_false_responds_to_all(self):
+        """MATTERMOST_REQUIRE_MENTION=false: respond to all channel messages."""
+        with patch.dict(os.environ, {"MATTERMOST_REQUIRE_MENTION": "false"}):
+            await self.adapter._handle_ws_event(self._make_event("hello"))
+            assert self.adapter.handle_message.called
+
+    @pytest.mark.asyncio
+    async def test_free_response_channel_responds_without_mention(self):
+        """Messages in free-response channels don't need @mention."""
+        with patch.dict(os.environ, {"MATTERMOST_FREE_RESPONSE_CHANNELS": "chan_456,chan_789"}):
+            os.environ.pop("MATTERMOST_REQUIRE_MENTION", None)
+            await self.adapter._handle_ws_event(self._make_event("hello", channel_id="chan_456"))
+            assert self.adapter.handle_message.called
+
+    @pytest.mark.asyncio
+    async def test_non_free_channel_still_requires_mention(self):
+        """Channels NOT in free-response list still require @mention."""
+        with patch.dict(os.environ, {"MATTERMOST_FREE_RESPONSE_CHANNELS": "chan_789"}):
+            os.environ.pop("MATTERMOST_REQUIRE_MENTION", None)
+            await self.adapter._handle_ws_event(self._make_event("hello", channel_id="chan_456"))
+            assert not self.adapter.handle_message.called
+
+    @pytest.mark.asyncio
+    async def test_dm_always_responds(self):
+        """DMs (channel_type=D) always respond regardless of mention settings."""
+        with patch.dict(os.environ, {}, clear=False):
+            os.environ.pop("MATTERMOST_REQUIRE_MENTION", None)
+            await self.adapter._handle_ws_event(self._make_event("hello", channel_type="D"))
+            assert self.adapter.handle_message.called
+
+    @pytest.mark.asyncio
+    async def test_mention_stripped_from_text(self):
+        """@mention is stripped from message text."""
+        with patch.dict(os.environ, {}, clear=False):
+            os.environ.pop("MATTERMOST_REQUIRE_MENTION", None)
+            await self.adapter._handle_ws_event(
+                self._make_event("@hermes-bot what is 2+2")
+            )
+            assert self.adapter.handle_message.called
+            msg = self.adapter.handle_message.call_args[0][0]
+            assert "@hermes-bot" not in msg.text
+            assert "2+2" in msg.text
+
+
 # ---------------------------------------------------------------------------
 # File upload (send_image)
 # ---------------------------------------------------------------------------
@@ -0,0 +1,722 @@
+"""
+Tests for media download retry logic added in PR #2982.
+
+Covers:
+- gateway/platforms/base.py:       cache_image_from_url
+- gateway/platforms/slack.py:      SlackAdapter._download_slack_file
+                                    SlackAdapter._download_slack_file_bytes
+- gateway/platforms/mattermost.py: MattermostAdapter._send_url_as_file
+
+All async tests use asyncio.run() directly — pytest-asyncio is not installed
+in this environment.
+"""
+
+import asyncio
+import sys
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+import httpx
+
+# ---------------------------------------------------------------------------
+# Helpers for building httpx exceptions
+# ---------------------------------------------------------------------------
+
+def _make_http_status_error(status_code: int) -> httpx.HTTPStatusError:
+    request = httpx.Request("GET", "http://example.com/img.jpg")
+    response = httpx.Response(status_code=status_code, request=request)
+    return httpx.HTTPStatusError(
+        f"HTTP {status_code}", request=request, response=response
+    )
+
+
+def _make_timeout_error() -> httpx.TimeoutException:
+    return httpx.TimeoutException("timed out")
+
+
+# ---------------------------------------------------------------------------
+# cache_image_from_url (base.py)
+# ---------------------------------------------------------------------------
+
+class TestCacheImageFromUrl:
+    """Tests for gateway.platforms.base.cache_image_from_url"""
+
+    def test_success_on_first_attempt(self, tmp_path, monkeypatch):
+        """A clean 200 response caches the image and returns a path."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+
+        fake_response = MagicMock()
+        fake_response.content = b"\xff\xd8\xff fake jpeg"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(return_value=fake_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client):
+                from gateway.platforms.base import cache_image_from_url
+                return await cache_image_from_url(
+                    "http://example.com/img.jpg", ext=".jpg"
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".jpg")
+        mock_client.get.assert_called_once()
+
+    def test_retries_on_timeout_then_succeeds(self, tmp_path, monkeypatch):
+        """A timeout on the first attempt is retried; second attempt succeeds."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+
+        fake_response = MagicMock()
+        fake_response.content = b"image data"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_timeout_error(), fake_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        mock_sleep = AsyncMock()
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                from gateway.platforms.base import cache_image_from_url
+                return await cache_image_from_url(
+                    "http://example.com/img.jpg", ext=".jpg", retries=2
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".jpg")
+        assert mock_client.get.call_count == 2
+        mock_sleep.assert_called_once()
+
+    def test_retries_on_429_then_succeeds(self, tmp_path, monkeypatch):
+        """A 429 response on the first attempt is retried; second attempt succeeds."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+
+        ok_response = MagicMock()
+        ok_response.content = b"image data"
+        ok_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_http_status_error(429), ok_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                from gateway.platforms.base import cache_image_from_url
+                return await cache_image_from_url(
+                    "http://example.com/img.jpg", ext=".jpg", retries=2
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".jpg")
+        assert mock_client.get.call_count == 2
+
+    def test_raises_after_max_retries_exhausted(self, tmp_path, monkeypatch):
+        """Timeout on every attempt raises after all retries are consumed."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_timeout_error())
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                from gateway.platforms.base import cache_image_from_url
+                await cache_image_from_url(
+                    "http://example.com/img.jpg", ext=".jpg", retries=2
+                )
+
+        with pytest.raises(httpx.TimeoutException):
+            asyncio.run(run())
+
+        # 3 total calls: initial + 2 retries
+        assert mock_client.get.call_count == 3
+
+    def test_non_retryable_4xx_raises_immediately(self, tmp_path, monkeypatch):
+        """A 404 (non-retryable) is raised immediately without any retry."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+
+        mock_sleep = AsyncMock()
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_http_status_error(404))
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                from gateway.platforms.base import cache_image_from_url
+                await cache_image_from_url(
+                    "http://example.com/img.jpg", ext=".jpg", retries=2
+                )
+
+        with pytest.raises(httpx.HTTPStatusError):
+            asyncio.run(run())
+
+        # Only 1 attempt, no sleep
+        assert mock_client.get.call_count == 1
+        mock_sleep.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# cache_audio_from_url (base.py)
+# ---------------------------------------------------------------------------
+
+class TestCacheAudioFromUrl:
+    """Tests for gateway.platforms.base.cache_audio_from_url"""
+
+    def test_success_on_first_attempt(self, tmp_path, monkeypatch):
+        """A clean 200 response caches the audio and returns a path."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        fake_response = MagicMock()
+        fake_response.content = b"\x00\x01 fake audio"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(return_value=fake_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client):
+                from gateway.platforms.base import cache_audio_from_url
+                return await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg"
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".ogg")
+        mock_client.get.assert_called_once()
+
+    def test_retries_on_timeout_then_succeeds(self, tmp_path, monkeypatch):
+        """A timeout on the first attempt is retried; second attempt succeeds."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        fake_response = MagicMock()
+        fake_response.content = b"audio data"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_timeout_error(), fake_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        mock_sleep = AsyncMock()
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                from gateway.platforms.base import cache_audio_from_url
+                return await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg", retries=2
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".ogg")
+        assert mock_client.get.call_count == 2
+        mock_sleep.assert_called_once()
+
+    def test_retries_on_429_then_succeeds(self, tmp_path, monkeypatch):
+        """A 429 response on the first attempt is retried; second attempt succeeds."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        ok_response = MagicMock()
+        ok_response.content = b"audio data"
+        ok_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_http_status_error(429), ok_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                from gateway.platforms.base import cache_audio_from_url
+                return await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg", retries=2
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".ogg")
+        assert mock_client.get.call_count == 2
+
+    def test_retries_on_500_then_succeeds(self, tmp_path, monkeypatch):
+        """A 500 response on the first attempt is retried; second attempt succeeds."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        ok_response = MagicMock()
+        ok_response.content = b"audio data"
+        ok_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_http_status_error(500), ok_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                from gateway.platforms.base import cache_audio_from_url
+                return await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg", retries=2
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".ogg")
+        assert mock_client.get.call_count == 2
+
+    def test_raises_after_max_retries_exhausted(self, tmp_path, monkeypatch):
+        """Timeout on every attempt raises after all retries are consumed."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_timeout_error())
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                from gateway.platforms.base import cache_audio_from_url
+                await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg", retries=2
+                )
+
+        with pytest.raises(httpx.TimeoutException):
+            asyncio.run(run())
+
+        # 3 total calls: initial + 2 retries
+        assert mock_client.get.call_count == 3
+
+    def test_non_retryable_4xx_raises_immediately(self, tmp_path, monkeypatch):
+        """A 404 (non-retryable) is raised immediately without any retry."""
+        monkeypatch.setattr("gateway.platforms.base.AUDIO_CACHE_DIR", tmp_path / "audio")
+
+        mock_sleep = AsyncMock()
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_http_status_error(404))
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                from gateway.platforms.base import cache_audio_from_url
+                await cache_audio_from_url(
+                    "http://example.com/voice.ogg", ext=".ogg", retries=2
+                )
+
+        with pytest.raises(httpx.HTTPStatusError):
+            asyncio.run(run())
+
+        # Only 1 attempt, no sleep
+        assert mock_client.get.call_count == 1
+        mock_sleep.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# Slack mock setup (mirrors existing test_slack.py approach)
+# ---------------------------------------------------------------------------
+
+def _ensure_slack_mock():
+    if "slack_bolt" in sys.modules and hasattr(sys.modules["slack_bolt"], "__file__"):
+        return
+    slack_bolt = MagicMock()
+    slack_bolt.async_app.AsyncApp = MagicMock
+    slack_bolt.adapter.socket_mode.async_handler.AsyncSocketModeHandler = MagicMock
+    slack_sdk = MagicMock()
+    slack_sdk.web.async_client.AsyncWebClient = MagicMock
+    for name, mod in [
+        ("slack_bolt", slack_bolt),
+        ("slack_bolt.async_app", slack_bolt.async_app),
+        ("slack_bolt.adapter", slack_bolt.adapter),
+        ("slack_bolt.adapter.socket_mode", slack_bolt.adapter.socket_mode),
+        ("slack_bolt.adapter.socket_mode.async_handler",
+         slack_bolt.adapter.socket_mode.async_handler),
+        ("slack_sdk", slack_sdk),
+        ("slack_sdk.web", slack_sdk.web),
+        ("slack_sdk.web.async_client", slack_sdk.web.async_client),
+    ]:
+        sys.modules.setdefault(name, mod)
+
+
+_ensure_slack_mock()
+
+import gateway.platforms.slack as _slack_mod  # noqa: E402
+_slack_mod.SLACK_AVAILABLE = True
+
+from gateway.platforms.slack import SlackAdapter  # noqa: E402
+from gateway.config import Platform, PlatformConfig  # noqa: E402
+
+
+def _make_slack_adapter():
+    config = PlatformConfig(enabled=True, token="xoxb-fake-token")
+    adapter = SlackAdapter(config)
+    adapter._app = MagicMock()
+    adapter._app.client = AsyncMock()
+    adapter._bot_user_id = "U_BOT"
+    adapter._running = True
+    return adapter
+
+
+# ---------------------------------------------------------------------------
+# SlackAdapter._download_slack_file
+# ---------------------------------------------------------------------------
+
+class TestSlackDownloadSlackFile:
+    """Tests for SlackAdapter._download_slack_file"""
+
+    def test_success_on_first_attempt(self, tmp_path, monkeypatch):
+        """Successful download on first try returns a cached file path."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+        adapter = _make_slack_adapter()
+
+        fake_response = MagicMock()
+        fake_response.content = b"fake image bytes"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(return_value=fake_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client):
+                return await adapter._download_slack_file(
+                    "https://files.slack.com/img.jpg", ext=".jpg"
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".jpg")
+        mock_client.get.assert_called_once()
+
+    def test_retries_on_timeout_then_succeeds(self, tmp_path, monkeypatch):
+        """Timeout on first attempt triggers retry; success on second."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+        adapter = _make_slack_adapter()
+
+        fake_response = MagicMock()
+        fake_response.content = b"image bytes"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_timeout_error(), fake_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        mock_sleep = AsyncMock()
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                return await adapter._download_slack_file(
+                    "https://files.slack.com/img.jpg", ext=".jpg"
+                )
+
+        path = asyncio.run(run())
+        assert path.endswith(".jpg")
+        assert mock_client.get.call_count == 2
+        mock_sleep.assert_called_once()
+
+    def test_raises_after_max_retries(self, tmp_path, monkeypatch):
+        """Timeout on every attempt eventually raises after 3 total tries."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+        adapter = _make_slack_adapter()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_timeout_error())
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                await adapter._download_slack_file(
+                    "https://files.slack.com/img.jpg", ext=".jpg"
+                )
+
+        with pytest.raises(httpx.TimeoutException):
+            asyncio.run(run())
+
+        assert mock_client.get.call_count == 3
+
+    def test_non_retryable_403_raises_immediately(self, tmp_path, monkeypatch):
+        """A 403 is not retried; it raises immediately."""
+        monkeypatch.setattr("gateway.platforms.base.IMAGE_CACHE_DIR", tmp_path / "img")
+        adapter = _make_slack_adapter()
+
+        mock_sleep = AsyncMock()
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_http_status_error(403))
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", mock_sleep):
+                await adapter._download_slack_file(
+                    "https://files.slack.com/img.jpg", ext=".jpg"
+                )
+
+        with pytest.raises(httpx.HTTPStatusError):
+            asyncio.run(run())
+
+        assert mock_client.get.call_count == 1
+        mock_sleep.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# SlackAdapter._download_slack_file_bytes
+# ---------------------------------------------------------------------------
+
+class TestSlackDownloadSlackFileBytes:
+    """Tests for SlackAdapter._download_slack_file_bytes"""
+
+    def test_success_returns_bytes(self):
+        """Successful download returns raw bytes."""
+        adapter = _make_slack_adapter()
+
+        fake_response = MagicMock()
+        fake_response.content = b"raw bytes here"
+        fake_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(return_value=fake_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client):
+                return await adapter._download_slack_file_bytes(
+                    "https://files.slack.com/file.bin"
+                )
+
+        result = asyncio.run(run())
+        assert result == b"raw bytes here"
+
+    def test_retries_on_429_then_succeeds(self):
+        """429 on first attempt is retried; raw bytes returned on second."""
+        adapter = _make_slack_adapter()
+
+        ok_response = MagicMock()
+        ok_response.content = b"final bytes"
+        ok_response.raise_for_status = MagicMock()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(
+            side_effect=[_make_http_status_error(429), ok_response]
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                return await adapter._download_slack_file_bytes(
+                    "https://files.slack.com/file.bin"
+                )
+
+        result = asyncio.run(run())
+        assert result == b"final bytes"
+        assert mock_client.get.call_count == 2
+
+    def test_raises_after_max_retries(self):
+        """Persistent timeouts raise after all 3 attempts are exhausted."""
+        adapter = _make_slack_adapter()
+
+        mock_client = AsyncMock()
+        mock_client.get = AsyncMock(side_effect=_make_timeout_error())
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        async def run():
+            with patch("httpx.AsyncClient", return_value=mock_client), \
+                 patch("asyncio.sleep", new_callable=AsyncMock):
+                await adapter._download_slack_file_bytes(
+                    "https://files.slack.com/file.bin"
+                )
+
+        with pytest.raises(httpx.TimeoutException):
+            asyncio.run(run())
+
+        assert mock_client.get.call_count == 3
+
+
+# ---------------------------------------------------------------------------
+# MattermostAdapter._send_url_as_file
+# ---------------------------------------------------------------------------
+
+def _make_mm_adapter():
+    """Build a minimal MattermostAdapter with mocked internals."""
+    from gateway.platforms.mattermost import MattermostAdapter
+    config = PlatformConfig(
+        enabled=True, token="mm-token-fake",
+        extra={"url": "https://mm.example.com"},
+    )
+    adapter = MattermostAdapter(config)
+    adapter._session = MagicMock()
+    adapter._upload_file = AsyncMock(return_value="file-id-123")
+    adapter._api_post = AsyncMock(return_value={"id": "post-id-abc"})
+    adapter.send = AsyncMock(return_value=MagicMock(success=True))
+    return adapter
+
+
+def _make_aiohttp_resp(status: int, content: bytes = b"file bytes",
+                       content_type: str = "image/jpeg"):
+    """Build a context-manager mock for an aiohttp response."""
+    resp = MagicMock()
+    resp.status = status
+    resp.content_type = content_type
+    resp.read = AsyncMock(return_value=content)
+    resp.__aenter__ = AsyncMock(return_value=resp)
+    resp.__aexit__ = AsyncMock(return_value=False)
+    return resp
+
+
+class TestMattermostSendUrlAsFile:
+    """Tests for MattermostAdapter._send_url_as_file"""
+
+    def test_success_on_first_attempt(self):
+        """200 on first attempt → file uploaded and post created."""
+        adapter = _make_mm_adapter()
+        resp = _make_aiohttp_resp(200)
+        adapter._session.get = MagicMock(return_value=resp)
+
+        async def run():
+            with patch("asyncio.sleep", new_callable=AsyncMock):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", "caption", None
+                )
+
+        result = asyncio.run(run())
+        assert result.success
+        adapter._upload_file.assert_called_once()
+        adapter._api_post.assert_called_once()
+
+    def test_retries_on_429_then_succeeds(self):
+        """429 on first attempt is retried; 200 on second attempt succeeds."""
+        adapter = _make_mm_adapter()
+
+        resp_429 = _make_aiohttp_resp(429)
+        resp_200 = _make_aiohttp_resp(200)
+        adapter._session.get = MagicMock(side_effect=[resp_429, resp_200])
+
+        mock_sleep = AsyncMock()
+
+        async def run():
+            with patch("asyncio.sleep", mock_sleep):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", None, None
+                )
+
+        result = asyncio.run(run())
+        assert result.success
+        assert adapter._session.get.call_count == 2
+        mock_sleep.assert_called_once()
+
+    def test_retries_on_500_then_succeeds(self):
+        """5xx on first attempt is retried; 200 on second attempt succeeds."""
+        adapter = _make_mm_adapter()
+
+        resp_500 = _make_aiohttp_resp(500)
+        resp_200 = _make_aiohttp_resp(200)
+        adapter._session.get = MagicMock(side_effect=[resp_500, resp_200])
+
+        async def run():
+            with patch("asyncio.sleep", new_callable=AsyncMock):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", None, None
+                )
+
+        result = asyncio.run(run())
+        assert result.success
+        assert adapter._session.get.call_count == 2
+
+    def test_falls_back_to_text_after_max_retries_on_5xx(self):
+        """Three consecutive 500s exhaust retries; falls back to send() with URL text."""
+        adapter = _make_mm_adapter()
+
+        resp_500 = _make_aiohttp_resp(500)
+        adapter._session.get = MagicMock(return_value=resp_500)
+
+        async def run():
+            with patch("asyncio.sleep", new_callable=AsyncMock):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", "my caption", None
+                )
+
+        asyncio.run(run())
+
+        adapter.send.assert_called_once()
+        text_arg = adapter.send.call_args[0][1]
+        assert "http://cdn.example.com/img.png" in text_arg
+
+    def test_falls_back_on_client_error(self):
+        """aiohttp.ClientError on every attempt falls back to send() with URL."""
+        import aiohttp
+
+        adapter = _make_mm_adapter()
+
+        error_resp = MagicMock()
+        error_resp.__aenter__ = AsyncMock(
+            side_effect=aiohttp.ClientConnectionError("connection refused")
+        )
+        error_resp.__aexit__ = AsyncMock(return_value=False)
+        adapter._session.get = MagicMock(return_value=error_resp)
+
+        async def run():
+            with patch("asyncio.sleep", new_callable=AsyncMock):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", None, None
+                )
+
+        asyncio.run(run())
+
+        adapter.send.assert_called_once()
+        text_arg = adapter.send.call_args[0][1]
+        assert "http://cdn.example.com/img.png" in text_arg
+
+    def test_non_retryable_404_falls_back_immediately(self):
+        """404 is non-retryable (< 500, != 429); send() is called right away."""
+        adapter = _make_mm_adapter()
+
+        resp_404 = _make_aiohttp_resp(404)
+        adapter._session.get = MagicMock(return_value=resp_404)
+
+        mock_sleep = AsyncMock()
+
+        async def run():
+            with patch("asyncio.sleep", mock_sleep):
+                return await adapter._send_url_as_file(
+                    "C123", "http://cdn.example.com/img.png", None, None
+                )
+
+        asyncio.run(run())
+
+        adapter.send.assert_called_once()
+        # No sleep — fell back on first attempt
+        mock_sleep.assert_not_called()
+        assert adapter._session.get.call_count == 1
@@ -62,6 +62,18 @@ class TestMessageEventGetCommand:
        event = MessageEvent(text="/")
        assert event.get_command() == ""

+    def test_command_with_at_botname(self):
+        event = MessageEvent(text="/new@TigerNanoBot")
+        assert event.get_command() == "new"
+
+    def test_command_with_at_botname_and_args(self):
+        event = MessageEvent(text="/compress@TigerNanoBot")
+        assert event.get_command() == "compress"
+
+    def test_command_mixed_case_with_at_botname(self):
+        event = MessageEvent(text="/RESET@TigerNanoBot")
+        assert event.get_command() == "reset"
+

 class TestMessageEventGetCommandArgs:
    def test_command_with_args(self):
@@ -344,6 +344,7 @@ class TestRuntimeDisconnectQueuing:
    async def test_retryable_runtime_error_queued_for_reconnect(self):
        """Retryable runtime errors should add the platform to _failed_platforms."""
        runner = _make_runner()
+        runner.stop = AsyncMock()

        adapter = StubAdapter(succeed=True)
        adapter._set_fatal_error("network_error", "DNS failure", retryable=True)
@@ -371,8 +372,12 @@ class TestRuntimeDisconnectQueuing:
        assert Platform.TELEGRAM not in runner._failed_platforms

    @pytest.mark.asyncio
-    async def test_retryable_error_prevents_shutdown_when_queued(self):
-        """Gateway should not shut down if failed platforms are queued for reconnection."""
+    async def test_retryable_error_exits_for_service_restart_when_all_down(self):
+        """Gateway should exit with failure when all platforms fail with retryable errors.
+
+        This lets systemd Restart=on-failure restart the process, which is more
+        reliable than in-process background reconnection after exhausted retries.
+        """
        runner = _make_runner()
        runner.stop = AsyncMock()

@@ -382,7 +387,28 @@ class TestRuntimeDisconnectQueuing:

        await runner._handle_adapter_fatal_error(adapter)

-        # stop() should NOT have been called since we have platforms queued
+        # stop() SHOULD be called — gateway exits for systemd restart
+        runner.stop.assert_called_once()
+        assert runner._exit_with_failure is True
+        assert Platform.TELEGRAM in runner._failed_platforms
+
+    @pytest.mark.asyncio
+    async def test_retryable_error_no_exit_when_other_adapters_still_connected(self):
+        """Gateway should NOT exit if some adapters are still connected."""
+        runner = _make_runner()
+        runner.stop = AsyncMock()
+
+        failing_adapter = StubAdapter(succeed=True)
+        failing_adapter._set_fatal_error("network_error", "DNS failure", retryable=True)
+        runner.adapters[Platform.TELEGRAM] = failing_adapter
+
+        # Another adapter is still connected
+        healthy_adapter = StubAdapter(succeed=True)
+        runner.adapters[Platform.DISCORD] = healthy_adapter
+
+        await runner._handle_adapter_fatal_error(failing_adapter)
+
+        # stop() should NOT have been called — Discord is still up
        runner.stop.assert_not_called()
        assert Platform.TELEGRAM in runner._failed_platforms

@@ -14,8 +14,8 @@ from gateway.session import SessionSource


 class ProgressCaptureAdapter(BasePlatformAdapter):
-    def __init__(self):
-        super().__init__(PlatformConfig(enabled=True, token="fake-token"), Platform.TELEGRAM)
+    def __init__(self, platform=Platform.TELEGRAM):
+        super().__init__(PlatformConfig(enabled=True, token="***"), platform)
        self.sent = []
        self.edits = []
        self.typing = []
@@ -76,7 +76,7 @@ def _make_runner(adapter):
    GatewayRunner = gateway_run.GatewayRunner

    runner = object.__new__(GatewayRunner)
-    runner.adapters = {Platform.TELEGRAM: adapter}
+    runner.adapters = {adapter.platform: adapter}
    runner._voice_mode = {}
    runner._prefill_messages = []
    runner._ephemeral_system_prompt = ""
@@ -133,3 +133,87 @@ async def test_run_agent_progress_stays_in_originating_topic(monkeypatch, tmp_pa
    ]
    assert adapter.edits
    assert all(call["metadata"] == {"thread_id": "17585"} for call in adapter.typing)
+
+
+@pytest.mark.asyncio
+async def test_run_agent_progress_does_not_use_event_message_id_for_telegram_dm(monkeypatch, tmp_path):
+    """Telegram DM progress must not reuse event message id as thread metadata."""
+    monkeypatch.setenv("HERMES_TOOL_PROGRESS_MODE", "all")
+
+    fake_dotenv = types.ModuleType("dotenv")
+    fake_dotenv.load_dotenv = lambda *args, **kwargs: None
+    monkeypatch.setitem(sys.modules, "dotenv", fake_dotenv)
+
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = FakeAgent
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    adapter = ProgressCaptureAdapter(platform=Platform.TELEGRAM)
+    runner = _make_runner(adapter)
+    gateway_run = importlib.import_module("gateway.run")
+    monkeypatch.setattr(gateway_run, "_hermes_home", tmp_path)
+    monkeypatch.setattr(gateway_run, "_resolve_runtime_agent_kwargs", lambda: {"api_key": "***"})
+
+    source = SessionSource(
+        platform=Platform.TELEGRAM,
+        chat_id="12345",
+        chat_type="dm",
+        thread_id=None,
+    )
+
+    result = await runner._run_agent(
+        message="hello",
+        context_prompt="",
+        history=[],
+        source=source,
+        session_id="sess-2",
+        session_key="agent:main:telegram:dm:12345",
+        event_message_id="777",
+    )
+
+    assert result["final_response"] == "done"
+    assert adapter.sent
+    assert adapter.sent[0]["metadata"] is None
+    assert all(call["metadata"] is None for call in adapter.typing)
+
+
+@pytest.mark.asyncio
+async def test_run_agent_progress_uses_event_message_id_for_slack_dm(monkeypatch, tmp_path):
+    """Slack DM progress should keep event ts fallback threading."""
+    monkeypatch.setenv("HERMES_TOOL_PROGRESS_MODE", "all")
+
+    fake_dotenv = types.ModuleType("dotenv")
+    fake_dotenv.load_dotenv = lambda *args, **kwargs: None
+    monkeypatch.setitem(sys.modules, "dotenv", fake_dotenv)
+
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = FakeAgent
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    adapter = ProgressCaptureAdapter(platform=Platform.SLACK)
+    runner = _make_runner(adapter)
+    gateway_run = importlib.import_module("gateway.run")
+    monkeypatch.setattr(gateway_run, "_hermes_home", tmp_path)
+    monkeypatch.setattr(gateway_run, "_resolve_runtime_agent_kwargs", lambda: {"api_key": "***"})
+
+    source = SessionSource(
+        platform=Platform.SLACK,
+        chat_id="D123",
+        chat_type="dm",
+        thread_id=None,
+    )
+
+    result = await runner._run_agent(
+        message="hello",
+        context_prompt="",
+        history=[],
+        source=source,
+        session_id="sess-3",
+        session_key="agent:main:slack:dm:D123",
+        event_message_id="1234567890.000001",
+    )
+
+    assert result["final_response"] == "done"
+    assert adapter.sent
+    assert adapter.sent[0]["metadata"] == {"thread_id": "1234567890.000001"}
+    assert all(call["metadata"] == {"thread_id": "1234567890.000001"} for call in adapter.typing)
@@ -89,7 +89,8 @@ async def test_runner_queues_retryable_runtime_fatal_for_reconnection(monkeypatc

    await runner._handle_adapter_fatal_error(adapter)

-    # Should NOT shut down — platform is queued for reconnection
-    runner.stop.assert_not_awaited()
+    # Should shut down with failure — systemd Restart=on-failure will restart
+    runner.stop.assert_awaited_once()
+    assert runner._exit_with_failure is True
    assert Platform.WHATSAPP in runner._failed_platforms
    assert runner._failed_platforms[Platform.WHATSAPP]["attempts"] == 0
@@ -76,7 +76,7 @@ def _ensure_telegram_mock():
    telegram_mod.constants.ChatType.CHANNEL = "channel"
    telegram_mod.constants.ChatType.PRIVATE = "private"

-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, telegram_mod)


@@ -0,0 +1,231 @@
+"""
+Tests for BasePlatformAdapter._send_with_retry and _is_retryable_error.
+
+Verifies that:
+- Transient network errors trigger retry with backoff
+- Permanent errors fall back to plain-text immediately (no retry)
+- User receives a delivery-failure notice when all retries are exhausted
+- Successful sends on retry return success
+- SendResult.retryable flag is respected
+"""
+import pytest
+from unittest.mock import AsyncMock, patch
+
+from gateway.platforms.base import BasePlatformAdapter, SendResult, _RETRYABLE_ERROR_PATTERNS
+from gateway.platforms.base import Platform, PlatformConfig
+
+
+# ---------------------------------------------------------------------------
+# Minimal concrete adapter for testing (no real network)
+# ---------------------------------------------------------------------------
+
+class _StubAdapter(BasePlatformAdapter):
+    def __init__(self):
+        cfg = PlatformConfig()
+        super().__init__(cfg, Platform.TELEGRAM)
+        self._send_results = []   # queue of SendResult to return per call
+        self._send_calls = []     # record of (chat_id, content) sent
+
+    def _next_result(self) -> SendResult:
+        if self._send_results:
+            return self._send_results.pop(0)
+        return SendResult(success=True, message_id="ok")
+
+    async def send(self, chat_id, content, reply_to=None, metadata=None, **kwargs) -> SendResult:
+        self._send_calls.append((chat_id, content))
+        return self._next_result()
+
+    async def connect(self) -> bool:
+        return True
+
+    async def disconnect(self) -> None:
+        pass
+
+    async def send_typing(self, chat_id, metadata=None) -> None:
+        pass
+
+    async def get_chat_info(self, chat_id):
+        return {"name": "test", "type": "direct", "chat_id": chat_id}
+
+
+# ---------------------------------------------------------------------------
+# _is_retryable_error
+# ---------------------------------------------------------------------------
+
+class TestIsRetryableError:
+    def test_none_is_not_retryable(self):
+        assert not _StubAdapter._is_retryable_error(None)
+
+    def test_empty_string_is_not_retryable(self):
+        assert not _StubAdapter._is_retryable_error("")
+
+    @pytest.mark.parametrize("pattern", _RETRYABLE_ERROR_PATTERNS)
+    def test_known_pattern_is_retryable(self, pattern):
+        assert _StubAdapter._is_retryable_error(f"httpx.{pattern.title()}: connection dropped")
+
+    def test_permission_error_not_retryable(self):
+        assert not _StubAdapter._is_retryable_error("Forbidden: bot was blocked by the user")
+
+    def test_bad_request_not_retryable(self):
+        assert not _StubAdapter._is_retryable_error("Bad Request: can't parse entities")
+
+    def test_case_insensitive(self):
+        assert _StubAdapter._is_retryable_error("CONNECTERROR: host unreachable")
+
+
+# ---------------------------------------------------------------------------
+# _send_with_retry — success on first attempt
+# ---------------------------------------------------------------------------
+
+class TestSendWithRetrySuccess:
+    @pytest.mark.asyncio
+    async def test_success_first_attempt(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [SendResult(success=True, message_id="123")]
+        result = await adapter._send_with_retry("chat1", "hello")
+        assert result.success
+        assert len(adapter._send_calls) == 1
+
+    @pytest.mark.asyncio
+    async def test_returns_message_id(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [SendResult(success=True, message_id="abc")]
+        result = await adapter._send_with_retry("chat1", "hi")
+        assert result.message_id == "abc"
+
+
+# ---------------------------------------------------------------------------
+# _send_with_retry — network error with successful retry
+# ---------------------------------------------------------------------------
+
+class TestSendWithRetryNetworkRetry:
+    @pytest.mark.asyncio
+    async def test_retries_on_connect_error_and_succeeds(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="httpx.ConnectError: connection refused"),
+            SendResult(success=True, message_id="ok"),
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=2, base_delay=0)
+        assert result.success
+        assert len(adapter._send_calls) == 2  # initial + 1 retry
+
+    @pytest.mark.asyncio
+    async def test_retries_on_timeout_and_succeeds(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="ReadTimeout: request timed out"),
+            SendResult(success=False, error="ReadTimeout: request timed out"),
+            SendResult(success=True, message_id="ok"),
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=3, base_delay=0)
+        assert result.success
+        assert len(adapter._send_calls) == 3
+
+    @pytest.mark.asyncio
+    async def test_retryable_flag_respected(self):
+        """SendResult.retryable=True should trigger retry even if error string doesn't match."""
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="internal platform error", retryable=True),
+            SendResult(success=True, message_id="ok"),
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=2, base_delay=0)
+        assert result.success
+        assert len(adapter._send_calls) == 2
+
+    @pytest.mark.asyncio
+    async def test_network_to_nonnetwork_transition_falls_back_to_plaintext(self):
+        """If error switches from network to formatting mid-retry, fall through to plain-text fallback."""
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="httpx.ConnectError: host unreachable"),
+            SendResult(success=False, error="Bad Request: can't parse entities"),
+            SendResult(success=True, message_id="fallback_ok"),  # plain-text fallback
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "**bold**", max_retries=2, base_delay=0)
+        assert result.success
+        # 3 calls: initial (network) + 1 retry (non-network, breaks loop) + plain-text fallback
+        assert len(adapter._send_calls) == 3
+        assert "plain text" in adapter._send_calls[-1][1].lower()
+
+
+# ---------------------------------------------------------------------------
+# _send_with_retry — all retries exhausted → user notification
+# ---------------------------------------------------------------------------
+
+class TestSendWithRetryExhausted:
+    @pytest.mark.asyncio
+    async def test_sends_user_notice_after_exhaustion(self):
+        adapter = _StubAdapter()
+        network_err = SendResult(success=False, error="httpx.ConnectError: host unreachable")
+        # initial + 2 retries + notice attempt
+        adapter._send_results = [network_err, network_err, network_err, SendResult(success=True)]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=2, base_delay=0)
+        # Result is the last failed one (before notice)
+        assert not result.success
+        # 4 total calls: 1 initial + 2 retries + 1 notice
+        assert len(adapter._send_calls) == 4
+        # The notice content should mention delivery failure
+        notice_content = adapter._send_calls[-1][1]
+        assert "delivery failed" in notice_content.lower() or "Message delivery failed" in notice_content
+
+    @pytest.mark.asyncio
+    async def test_notice_send_exception_doesnt_propagate(self):
+        """If the notice itself throws, _send_with_retry should not raise."""
+        adapter = _StubAdapter()
+        network_err = SendResult(success=False, error="ConnectError")
+        adapter._send_results = [network_err, network_err, network_err]
+
+        original_send = adapter.send
+        call_count = [0]
+
+        async def send_with_notice_failure(chat_id, content, **kwargs):
+            call_count[0] += 1
+            if call_count[0] > 3:
+                raise RuntimeError("notice send also failed")
+            return network_err
+
+        adapter.send = send_with_notice_failure
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=2, base_delay=0)
+        assert not result.success  # still failed, but no exception raised
+
+
+# ---------------------------------------------------------------------------
+# _send_with_retry — non-network failure → plain-text fallback (no retry)
+# ---------------------------------------------------------------------------
+
+class TestSendWithRetryFallback:
+    @pytest.mark.asyncio
+    async def test_non_network_error_falls_back_immediately(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="Bad Request: can't parse entities"),
+            SendResult(success=True, message_id="fallback_ok"),
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock) as mock_sleep:
+            result = await adapter._send_with_retry("chat1", "**bold**", max_retries=2, base_delay=0)
+        # No sleep — no retry loop for non-network errors
+        mock_sleep.assert_not_called()
+        assert result.success
+        assert len(adapter._send_calls) == 2
+        # Fallback content should be plain-text notice
+        assert "plain text" in adapter._send_calls[1][1].lower()
+
+    @pytest.mark.asyncio
+    async def test_fallback_failure_logged_but_not_raised(self):
+        adapter = _StubAdapter()
+        adapter._send_results = [
+            SendResult(success=False, error="Forbidden: bot blocked"),
+            SendResult(success=False, error="Forbidden: bot blocked"),
+        ]
+        with patch("asyncio.sleep", new_callable=AsyncMock):
+            result = await adapter._send_with_retry("chat1", "hello", max_retries=2)
+        assert not result.success
+        assert len(adapter._send_calls) == 2  # original + fallback only
@@ -846,7 +846,7 @@ class TestLastPromptTokens:

        store.update_session("k1", model="openai/gpt-5.4")

-        store._db.update_token_counts.assert_called_once_with(
+        store._db.set_token_counts.assert_called_once_with(
            "s1",
            input_tokens=0,
            output_tokens=0,
@@ -858,4 +858,48 @@ class TestLastPromptTokens:
            billing_provider=None,
            billing_base_url=None,
            model="openai/gpt-5.4",
+            absolute=True,
        )
+
+
+class TestRewriteTranscriptPreservesReasoning:
+    """rewrite_transcript must not drop reasoning fields from SQLite."""
+
+    def test_reasoning_survives_rewrite(self, tmp_path):
+        from hermes_state import SessionDB
+
+        db = SessionDB(db_path=tmp_path / "test.db")
+        session_id = "reasoning-test"
+        db.create_session(session_id=session_id, source="cli")
+
+        # Insert a message WITH all three reasoning fields
+        db.append_message(
+            session_id=session_id,
+            role="assistant",
+            content="The answer is 42.",
+            reasoning="I need to think step by step.",
+            reasoning_details=[{"type": "summary", "text": "step by step"}],
+            codex_reasoning_items=[{"id": "r1", "type": "reasoning"}],
+        )
+
+        # Verify all three were stored
+        before = db.get_messages_as_conversation(session_id)
+        assert before[0].get("reasoning") == "I need to think step by step."
+        assert before[0].get("reasoning_details") == [{"type": "summary", "text": "step by step"}]
+        assert before[0].get("codex_reasoning_items") == [{"id": "r1", "type": "reasoning"}]
+
+        # Now simulate /retry: build the SessionStore and call rewrite_transcript
+        config = GatewayConfig()
+        with patch("gateway.session.SessionStore._ensure_loaded"):
+            store = SessionStore(sessions_dir=tmp_path, config=config)
+        store._db = db
+        store._loaded = True
+
+        # rewrite_transcript receives the messages that load_transcript returned
+        store.rewrite_transcript(session_id, before)
+
+        # Load again — all three reasoning fields must survive
+        after = db.get_messages_as_conversation(session_id)
+        assert after[0].get("reasoning") == "I need to think step by step."
+        assert after[0].get("reasoning_details") == [{"type": "summary", "text": "step by step"}]
+        assert after[0].get("codex_reasoning_items") == [{"id": "r1", "type": "reasoning"}]
@@ -304,8 +304,12 @@ async def test_session_hygiene_messages_stay_in_originating_topic(monkeypatch, t
    class FakeCompressAgent:
        def __init__(self, **kwargs):
            self.model = kwargs.get("model")
+            self.session_id = kwargs.get("session_id", "fake-session")
+            self._print_fn = None

        def _compress_context(self, messages, *_args, **_kwargs):
+            # Simulate real _compress_context: create a new session_id
+            self.session_id = f"{self.session_id}_compressed"
            return ([{"role": "assistant", "content": "compressed"}], None)

    fake_run_agent = types.ModuleType("run_agent")
@@ -0,0 +1,110 @@
+"""Tests for GatewayRunner._format_session_info — session config surfacing."""
+
+import pytest
+from unittest.mock import patch, MagicMock
+from pathlib import Path
+
+from gateway.run import GatewayRunner
+
+
+@pytest.fixture()
+def runner():
+    """Create a bare GatewayRunner without __init__."""
+    return GatewayRunner.__new__(GatewayRunner)
+
+
+def _patch_info(tmp_path, config_yaml, model, runtime):
+    """Return a context-manager stack that patches _format_session_info deps."""
+    cfg_path = tmp_path / "config.yaml"
+    if config_yaml is not None:
+        cfg_path.write_text(config_yaml)
+    return (
+        patch("gateway.run._hermes_home", tmp_path),
+        patch("gateway.run._resolve_gateway_model", return_value=model),
+        patch("gateway.run._resolve_runtime_agent_kwargs", return_value=runtime),
+    )
+
+
+class TestFormatSessionInfo:
+
+    def test_includes_model_name(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: anthropic/claude-opus-4.6\n  provider: openrouter\n",
+                                  "anthropic/claude-opus-4.6",
+                                  {"provider": "openrouter", "base_url": "https://openrouter.ai/api/v1", "api_key": "k"})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "claude-opus-4.6" in info
+
+    def test_includes_provider(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: test-model\n  provider: openrouter\n",
+                                  "test-model",
+                                  {"provider": "openrouter", "base_url": "", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "openrouter" in info
+
+    def test_config_context_length(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: test-model\n  context_length: 32768\n",
+                                  "test-model",
+                                  {"provider": "custom", "base_url": "", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "32K" in info
+        assert "config" in info
+
+    def test_default_fallback_hint(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: unknown-model-xyz\n",
+                                  "unknown-model-xyz",
+                                  {"provider": "", "base_url": "", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "128K" in info
+        assert "model.context_length" in info
+
+    def test_local_endpoint_shown(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(
+            tmp_path,
+            "model:\n  default: qwen3:8b\n  provider: custom\n  base_url: http://localhost:11434/v1\n  context_length: 8192\n",
+            "qwen3:8b",
+            {"provider": "custom", "base_url": "http://localhost:11434/v1", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "localhost:11434" in info
+        assert "8K" in info
+
+    def test_cloud_endpoint_hidden(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: test-model\n  provider: openrouter\n",
+                                  "test-model",
+                                  {"provider": "openrouter", "base_url": "https://openrouter.ai/api/v1", "api_key": "k"})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "Endpoint" not in info
+
+    def test_million_context_format(self, runner, tmp_path):
+        p1, p2, p3 = _patch_info(tmp_path, "model:\n  default: test-model\n  context_length: 1000000\n",
+                                  "test-model",
+                                  {"provider": "", "base_url": "", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "1.0M" in info
+
+    def test_missing_config(self, runner, tmp_path):
+        """No config.yaml should not crash."""
+        p1, p2, p3 = _patch_info(tmp_path, None,  # don't create config
+                                  "anthropic/claude-sonnet-4.6",
+                                  {"provider": "openrouter", "base_url": "", "api_key": ""})
+        with p1, p2, p3:
+            info = runner._format_session_info()
+        assert "Model" in info
+        assert "Context" in info
+
+    def test_runtime_resolution_failure_doesnt_crash(self, runner, tmp_path):
+        """If runtime resolution raises, should still produce output."""
+        cfg_path = tmp_path / "config.yaml"
+        cfg_path.write_text("model:\n  default: test-model\n  context_length: 4096\n")
+        with patch("gateway.run._hermes_home", tmp_path), \
+             patch("gateway.run._resolve_gateway_model", return_value="test-model"), \
+             patch("gateway.run._resolve_runtime_agent_kwargs", side_effect=RuntimeError("no creds")):
+            info = runner._format_session_info()
+        assert "4K" in info
+        assert "config" in info
@@ -0,0 +1,280 @@
+"""Tests for SSE client disconnect → agent task cancellation.
+
+When a streaming /v1/chat/completions client disconnects mid-stream
+(network drop, browser tab close), the agent is interrupted via
+agent.interrupt() so it stops making LLM API calls, and the asyncio
+task wrapper is cancelled.
+"""
+
+import asyncio
+import json
+import queue
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+def _make_adapter():
+    """Build a minimal APIServerAdapter with mocked internals."""
+    from gateway.platforms.api_server import APIServerAdapter
+    from gateway.config import PlatformConfig
+
+    config = PlatformConfig(enabled=True, token="test-key")
+    adapter = APIServerAdapter(config)
+    return adapter
+
+
+def _make_request():
+    """Build a mock aiohttp request."""
+    req = MagicMock()
+    req.headers = {}
+    return req
+
+
+# ---------------------------------------------------------------------------
+# Tests
+# ---------------------------------------------------------------------------
+
+class TestSSEAgentCancelOnDisconnect:
+    """gateway/platforms/api_server.py — _write_sse_chat_completion()"""
+
+    def test_agent_task_cancelled_on_client_disconnect(self):
+        """When response.write raises ConnectionResetError (client dropped),
+        the agent task must be cancelled."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+        stream_q.put("hello ")  # Some data already queued
+
+        # Agent task that runs forever (simulates a long LLM call)
+        agent_done = asyncio.Event()
+
+        async def fake_agent():
+            await agent_done.wait()
+            return {"final_response": "done"}, {"input_tokens": 10, "output_tokens": 5, "total_tokens": 15}
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+
+            # Mock response that raises ConnectionResetError on second write
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            call_count = 0
+
+            async def write_side_effect(data):
+                nonlocal call_count
+                call_count += 1
+                if call_count >= 2:
+                    raise ConnectionResetError("client disconnected")
+
+            mock_response.write = AsyncMock(side_effect=write_side_effect)
+            mock_response.prepare = AsyncMock()
+
+            with patch.object(type(adapter), '_write_sse_chat_completion',
+                              adapter._write_sse_chat_completion):
+                # Patch StreamResponse creation
+                with patch("gateway.platforms.api_server.web.StreamResponse",
+                           return_value=mock_response):
+                    await adapter._write_sse_chat_completion(
+                        _make_request(), "cmpl-123", "gpt-4", 1234567890,
+                        stream_q, agent_task,
+                    )
+
+            # The critical assertion: agent_task must be cancelled
+            assert agent_task.cancelled() or agent_task.done()
+            # Clean up
+            agent_done.set()
+
+        asyncio.run(run())
+
+    def test_agent_task_not_cancelled_on_normal_completion(self):
+        """On normal stream completion, agent task should NOT be cancelled."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+        stream_q.put("hello")
+        stream_q.put(None)  # End-of-stream sentinel
+
+        async def fake_agent():
+            return {"final_response": "done"}, {"input_tokens": 10, "output_tokens": 5, "total_tokens": 15}
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+            await asyncio.sleep(0)  # Let agent complete
+
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            mock_response.write = AsyncMock()
+            mock_response.prepare = AsyncMock()
+
+            with patch("gateway.platforms.api_server.web.StreamResponse",
+                       return_value=mock_response):
+                await adapter._write_sse_chat_completion(
+                    _make_request(), "cmpl-456", "gpt-4", 1234567890,
+                    stream_q, agent_task,
+                )
+
+            # Agent should have completed normally, not been cancelled
+            assert agent_task.done()
+            assert not agent_task.cancelled()
+
+        asyncio.run(run())
+
+    def test_broken_pipe_also_cancels_agent(self):
+        """BrokenPipeError (another disconnect variant) also cancels the task."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+
+        async def fake_agent():
+            await asyncio.sleep(999)  # Never completes
+            return {}, {}
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            mock_response.write = AsyncMock(side_effect=BrokenPipeError("pipe broken"))
+            mock_response.prepare = AsyncMock()
+
+            with patch("gateway.platforms.api_server.web.StreamResponse",
+                       return_value=mock_response):
+                await adapter._write_sse_chat_completion(
+                    _make_request(), "cmpl-789", "gpt-4", 1234567890,
+                    stream_q, agent_task,
+                )
+
+            assert agent_task.cancelled() or agent_task.done()
+
+        asyncio.run(run())
+
+    def test_already_done_task_not_cancelled_on_disconnect(self):
+        """If agent already finished before disconnect, don't try to cancel."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+        stream_q.put("data")
+
+        async def fake_agent():
+            return {"final_response": "done"}, {}
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+            await asyncio.sleep(0)  # Let agent complete
+
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            call_count = 0
+
+            async def write_side_effect(data):
+                nonlocal call_count
+                call_count += 1
+                if call_count >= 2:
+                    raise ConnectionResetError("late disconnect")
+
+            mock_response.write = AsyncMock(side_effect=write_side_effect)
+            mock_response.prepare = AsyncMock()
+
+            with patch("gateway.platforms.api_server.web.StreamResponse",
+                       return_value=mock_response):
+                await adapter._write_sse_chat_completion(
+                    _make_request(), "cmpl-done", "gpt-4", 1234567890,
+                    stream_q, agent_task,
+                )
+
+            # Task was already done — should not be cancelled
+            assert agent_task.done()
+            assert not agent_task.cancelled()
+
+        asyncio.run(run())
+
+    def test_agent_interrupt_called_on_disconnect(self):
+        """When the client disconnects, agent.interrupt() must be called
+        so the agent thread stops making LLM API calls."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+        stream_q.put("hello ")
+
+        agent_done = asyncio.Event()
+
+        async def fake_agent():
+            await agent_done.wait()
+            return {"final_response": "done"}, {}
+
+        # Mock agent with an interrupt method
+        mock_agent = MagicMock()
+        mock_agent.interrupt = MagicMock()
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+            agent_ref = [mock_agent]
+
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            call_count = 0
+
+            async def write_side_effect(data):
+                nonlocal call_count
+                call_count += 1
+                if call_count >= 2:
+                    raise ConnectionResetError("client disconnected")
+
+            mock_response.write = AsyncMock(side_effect=write_side_effect)
+            mock_response.prepare = AsyncMock()
+
+            with patch("gateway.platforms.api_server.web.StreamResponse",
+                       return_value=mock_response):
+                await adapter._write_sse_chat_completion(
+                    _make_request(), "cmpl-int", "gpt-4", 1234567890,
+                    stream_q, agent_task, agent_ref,
+                )
+
+            # agent.interrupt() must have been called
+            mock_agent.interrupt.assert_called_once_with("SSE client disconnected")
+            # Clean up
+            agent_done.set()
+
+        asyncio.run(run())
+
+    def test_agent_ref_none_still_cancels_task(self):
+        """When agent_ref is not provided (None), the task is still cancelled
+        on disconnect — just without the interrupt() call."""
+        adapter = _make_adapter()
+
+        stream_q = queue.Queue()
+
+        async def fake_agent():
+            await asyncio.sleep(999)
+            return {}, {}
+
+        async def run():
+            from aiohttp import web
+
+            agent_task = asyncio.ensure_future(fake_agent())
+
+            mock_response = AsyncMock(spec=web.StreamResponse)
+            mock_response.write = AsyncMock(side_effect=BrokenPipeError("gone"))
+            mock_response.prepare = AsyncMock()
+
+            with patch("gateway.platforms.api_server.web.StreamResponse",
+                       return_value=mock_response):
+                # No agent_ref passed — should still handle disconnect cleanly
+                await adapter._write_sse_chat_completion(
+                    _make_request(), "cmpl-noref", "gpt-4", 1234567890,
+                    stream_q, agent_task,
+                )
+
+            assert agent_task.cancelled() or agent_task.done()
+
+        asyncio.run(run())
@@ -20,7 +20,7 @@ def _ensure_telegram_mock():
    telegram_mod.constants.ChatType.CHANNEL = "channel"
    telegram_mod.constants.ChatType.PRIVATE = "private"

-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, telegram_mod)


@@ -29,6 +29,14 @@ _ensure_telegram_mock()
 from gateway.platforms.telegram import TelegramAdapter  # noqa: E402


+@pytest.fixture(autouse=True)
+def _no_auto_discovery(monkeypatch):
+    """Disable DoH auto-discovery so connect() uses the plain builder chain."""
+    async def _noop():
+        return []
+    monkeypatch.setattr("gateway.platforms.telegram.discover_fallback_ips", _noop)
+
+
@pytest.mark.asyncio
 async def test_connect_rejects_same_host_token_lock(monkeypatch):
    adapter = TelegramAdapter(PlatformConfig(enabled=True, token="secret-token"))
@@ -45,7 +45,7 @@ def _ensure_telegram_mock():
    telegram_mod.constants.ChatType.CHANNEL = "channel"
    telegram_mod.constants.ChatType.PRIVATE = "private"

-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, telegram_mod)


@@ -28,7 +28,7 @@ def _ensure_telegram_mock():
    mod.constants.ChatType.SUPERGROUP = "supergroup"
    mod.constants.ChatType.CHANNEL = "channel"
    mod.constants.ChatType.PRIVATE = "private"
-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, mod)


@@ -0,0 +1,644 @@
+"""Tests for gateway.platforms.telegram_network – fallback transport layer.
+
+Background
+----------
+api.telegram.org resolves to an IP (e.g. 149.154.166.110) that is unreachable
+from some networks.  The workaround: route TCP through a different IP in the
+same Telegram-owned 149.154.160.0/20 block (e.g. 149.154.167.220) while
+keeping TLS SNI and the Host header as api.telegram.org so Telegram's edge
+servers still accept the request.  This is the programmatic equivalent of:
+
+    curl --resolve api.telegram.org:443:149.154.167.220 https://api.telegram.org/bot<token>/getMe
+
+The TelegramFallbackTransport implements this: try the primary (DNS-resolved)
+path first, and on ConnectTimeout / ConnectError fall through to configured
+fallback IPs in order, then "stick" to whichever IP works.
+"""
+
+import httpx
+import pytest
+
+from gateway.platforms import telegram_network as tnet
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+class FakeTransport(httpx.AsyncBaseTransport):
+    """Records calls and raises / returns based on a host→action mapping."""
+
+    def __init__(self, calls, behavior):
+        self.calls = calls
+        self.behavior = behavior
+        self.closed = False
+
+    async def handle_async_request(self, request: httpx.Request) -> httpx.Response:
+        self.calls.append(
+            {
+                "url_host": request.url.host,
+                "host_header": request.headers.get("host"),
+                "sni_hostname": request.extensions.get("sni_hostname"),
+                "path": request.url.path,
+            }
+        )
+        action = self.behavior.get(request.url.host, "ok")
+        if action == "timeout":
+            raise httpx.ConnectTimeout("timed out")
+        if action == "connect_error":
+            raise httpx.ConnectError("connect error")
+        if isinstance(action, Exception):
+            raise action
+        return httpx.Response(200, request=request, text="ok")
+
+    async def aclose(self) -> None:
+        self.closed = True
+
+
+def _fake_transport_factory(calls, behavior):
+    """Returns a factory that creates FakeTransport instances."""
+    instances = []
+
+    def factory(**kwargs):
+        t = FakeTransport(calls, behavior)
+        instances.append(t)
+        return t
+
+    factory.instances = instances
+    return factory
+
+
+def _telegram_request(path="/botTOKEN/getMe"):
+    return httpx.Request("GET", f"https://api.telegram.org{path}")
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# IP parsing & validation
+# ═══════════════════════════════════════════════════════════════════════════
+
+class TestParseFallbackIpEnv:
+    def test_filters_invalid_and_ipv6(self, caplog):
+        ips = tnet.parse_fallback_ip_env("149.154.167.220, bad, 2001:67c:4e8:f004::9,149.154.167.220")
+        assert ips == ["149.154.167.220", "149.154.167.220"]
+        assert "Ignoring invalid Telegram fallback IP" in caplog.text
+        assert "Ignoring non-IPv4 Telegram fallback IP" in caplog.text
+
+    def test_none_returns_empty(self):
+        assert tnet.parse_fallback_ip_env(None) == []
+
+    def test_empty_string_returns_empty(self):
+        assert tnet.parse_fallback_ip_env("") == []
+
+    def test_whitespace_only_returns_empty(self):
+        assert tnet.parse_fallback_ip_env("  ,  , ") == []
+
+    def test_single_valid_ip(self):
+        assert tnet.parse_fallback_ip_env("149.154.167.220") == ["149.154.167.220"]
+
+    def test_multiple_valid_ips(self):
+        ips = tnet.parse_fallback_ip_env("149.154.167.220, 149.154.167.221")
+        assert ips == ["149.154.167.220", "149.154.167.221"]
+
+    def test_rejects_leading_zeros(self, caplog):
+        """Leading zeros are ambiguous (octal?) so ipaddress rejects them."""
+        ips = tnet.parse_fallback_ip_env("149.154.167.010")
+        assert ips == []
+        assert "Ignoring invalid" in caplog.text
+
+
+class TestNormalizeFallbackIps:
+    def test_deduplication_happens_at_transport_level(self):
+        """_normalize does not dedup; TelegramFallbackTransport.__init__ does."""
+        raw = ["149.154.167.220", "149.154.167.220"]
+        assert tnet._normalize_fallback_ips(raw) == ["149.154.167.220", "149.154.167.220"]
+
+    def test_empty_strings_skipped(self):
+        assert tnet._normalize_fallback_ips(["", "  ", "149.154.167.220"]) == ["149.154.167.220"]
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# Request rewriting
+# ═══════════════════════════════════════════════════════════════════════════
+
+class TestRewriteRequestForIp:
+    def test_preserves_host_and_sni(self):
+        request = _telegram_request()
+        rewritten = tnet._rewrite_request_for_ip(request, "149.154.167.220")
+
+        assert rewritten.url.host == "149.154.167.220"
+        assert rewritten.headers["host"] == "api.telegram.org"
+        assert rewritten.extensions["sni_hostname"] == "api.telegram.org"
+        assert rewritten.url.path == "/botTOKEN/getMe"
+
+    def test_preserves_method_and_path(self):
+        request = httpx.Request("POST", "https://api.telegram.org/botTOKEN/sendMessage")
+        rewritten = tnet._rewrite_request_for_ip(request, "149.154.167.220")
+
+        assert rewritten.method == "POST"
+        assert rewritten.url.path == "/botTOKEN/sendMessage"
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# Fallback transport – core behavior
+# ═══════════════════════════════════════════════════════════════════════════
+
+class TestFallbackTransport:
+    """Primary path fails → try fallback IPs → stick to whichever works."""
+
+    @pytest.mark.asyncio
+    async def test_falls_back_on_connect_timeout_and_becomes_sticky(self, monkeypatch):
+        calls = []
+        behavior = {"api.telegram.org": "timeout", "149.154.167.220": "ok"}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+        resp = await transport.handle_async_request(_telegram_request())
+
+        assert resp.status_code == 200
+        assert transport._sticky_ip == "149.154.167.220"
+        # First attempt was primary (api.telegram.org), second was fallback
+        assert calls[0]["url_host"] == "api.telegram.org"
+        assert calls[1]["url_host"] == "149.154.167.220"
+        assert calls[1]["host_header"] == "api.telegram.org"
+        assert calls[1]["sni_hostname"] == "api.telegram.org"
+
+        # Second request goes straight to sticky IP
+        calls.clear()
+        resp2 = await transport.handle_async_request(_telegram_request())
+        assert resp2.status_code == 200
+        assert calls[0]["url_host"] == "149.154.167.220"
+
+    @pytest.mark.asyncio
+    async def test_falls_back_on_connect_error(self, monkeypatch):
+        calls = []
+        behavior = {"api.telegram.org": "connect_error", "149.154.167.220": "ok"}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+        resp = await transport.handle_async_request(_telegram_request())
+
+        assert resp.status_code == 200
+        assert transport._sticky_ip == "149.154.167.220"
+
+    @pytest.mark.asyncio
+    async def test_does_not_fallback_on_non_connect_error(self, monkeypatch):
+        """Errors like ReadTimeout are not connection issues — don't retry."""
+        calls = []
+        behavior = {"api.telegram.org": httpx.ReadTimeout("read timeout"), "149.154.167.220": "ok"}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+
+        with pytest.raises(httpx.ReadTimeout):
+            await transport.handle_async_request(_telegram_request())
+
+        assert [c["url_host"] for c in calls] == ["api.telegram.org"]
+
+    @pytest.mark.asyncio
+    async def test_all_ips_fail_raises_last_error(self, monkeypatch):
+        calls = []
+        behavior = {"api.telegram.org": "timeout", "149.154.167.220": "timeout"}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+
+        with pytest.raises(httpx.ConnectTimeout):
+            await transport.handle_async_request(_telegram_request())
+
+        assert [c["url_host"] for c in calls] == ["api.telegram.org", "149.154.167.220"]
+        assert transport._sticky_ip is None
+
+    @pytest.mark.asyncio
+    async def test_multiple_fallback_ips_tried_in_order(self, monkeypatch):
+        calls = []
+        behavior = {
+            "api.telegram.org": "timeout",
+            "149.154.167.220": "timeout",
+            "149.154.167.221": "ok",
+        }
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220", "149.154.167.221"])
+        resp = await transport.handle_async_request(_telegram_request())
+
+        assert resp.status_code == 200
+        assert transport._sticky_ip == "149.154.167.221"
+        assert [c["url_host"] for c in calls] == [
+            "api.telegram.org",
+            "149.154.167.220",
+            "149.154.167.221",
+        ]
+
+    @pytest.mark.asyncio
+    async def test_sticky_ip_tried_first_but_falls_through_if_stale(self, monkeypatch):
+        """If the sticky IP stops working, the transport retries others."""
+        calls = []
+        behavior = {
+            "api.telegram.org": "timeout",
+            "149.154.167.220": "ok",
+            "149.154.167.221": "ok",
+        }
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220", "149.154.167.221"])
+
+        # First request: primary fails → .220 works → becomes sticky
+        await transport.handle_async_request(_telegram_request())
+        assert transport._sticky_ip == "149.154.167.220"
+
+        # Now .220 goes bad too
+        calls.clear()
+        behavior["149.154.167.220"] = "timeout"
+
+        resp = await transport.handle_async_request(_telegram_request())
+        assert resp.status_code == 200
+        # Tried sticky (.220) first, then fell through to .221
+        assert [c["url_host"] for c in calls] == ["149.154.167.220", "149.154.167.221"]
+        assert transport._sticky_ip == "149.154.167.221"
+
+
+class TestFallbackTransportPassthrough:
+    """Requests that don't need fallback behavior."""
+
+    @pytest.mark.asyncio
+    async def test_non_telegram_host_bypasses_fallback(self, monkeypatch):
+        calls = []
+        behavior = {}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+        request = httpx.Request("GET", "https://example.com/path")
+        resp = await transport.handle_async_request(request)
+
+        assert resp.status_code == 200
+        assert calls[0]["url_host"] == "example.com"
+        assert transport._sticky_ip is None
+
+    @pytest.mark.asyncio
+    async def test_empty_fallback_list_uses_primary_only(self, monkeypatch):
+        calls = []
+        behavior = {}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport([])
+        resp = await transport.handle_async_request(_telegram_request())
+
+        assert resp.status_code == 200
+        assert calls[0]["url_host"] == "api.telegram.org"
+
+    @pytest.mark.asyncio
+    async def test_primary_succeeds_no_fallback_needed(self, monkeypatch):
+        calls = []
+        behavior = {"api.telegram.org": "ok"}
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", _fake_transport_factory(calls, behavior))
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+        resp = await transport.handle_async_request(_telegram_request())
+
+        assert resp.status_code == 200
+        assert transport._sticky_ip is None
+        assert len(calls) == 1
+
+
+class TestFallbackTransportInit:
+    def test_deduplicates_fallback_ips(self, monkeypatch):
+        monkeypatch.setattr(
+            tnet.httpx, "AsyncHTTPTransport", lambda **kw: FakeTransport([], {})
+        )
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220", "149.154.167.220"])
+        assert transport._fallback_ips == ["149.154.167.220"]
+
+    def test_filters_invalid_ips_at_init(self, monkeypatch):
+        monkeypatch.setattr(
+            tnet.httpx, "AsyncHTTPTransport", lambda **kw: FakeTransport([], {})
+        )
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220", "not-an-ip"])
+        assert transport._fallback_ips == ["149.154.167.220"]
+
+    def test_uses_proxy_env_for_primary_and_fallback_transports(self, monkeypatch):
+        seen_kwargs = []
+
+        def factory(**kwargs):
+            seen_kwargs.append(kwargs.copy())
+            return FakeTransport([], {})
+
+        for key in ("HTTPS_PROXY", "HTTP_PROXY", "ALL_PROXY", "https_proxy", "http_proxy", "all_proxy"):
+            monkeypatch.delenv(key, raising=False)
+        monkeypatch.setenv("HTTPS_PROXY", "http://proxy.example:8080")
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", factory)
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220"])
+
+        assert transport._fallback_ips == ["149.154.167.220"]
+        assert len(seen_kwargs) == 2
+        assert all(kwargs["proxy"] == "http://proxy.example:8080" for kwargs in seen_kwargs)
+
+
+class TestFallbackTransportClose:
+    @pytest.mark.asyncio
+    async def test_aclose_closes_all_transports(self, monkeypatch):
+        factory = _fake_transport_factory([], {})
+        monkeypatch.setattr(tnet.httpx, "AsyncHTTPTransport", factory)
+
+        transport = tnet.TelegramFallbackTransport(["149.154.167.220", "149.154.167.221"])
+        await transport.aclose()
+
+        # 1 primary + 2 fallback transports
+        assert len(factory.instances) == 3
+        assert all(t.closed for t in factory.instances)
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# Config layer – TELEGRAM_FALLBACK_IPS env → config.extra
+# ═══════════════════════════════════════════════════════════════════════════
+
+class TestConfigFallbackIps:
+    def test_env_var_populates_config_extra(self, monkeypatch):
+        from gateway.config import GatewayConfig, Platform, PlatformConfig, _apply_env_overrides
+
+        monkeypatch.setenv("TELEGRAM_FALLBACK_IPS", "149.154.167.220,149.154.167.221")
+        config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="tok")})
+        _apply_env_overrides(config)
+
+        assert config.platforms[Platform.TELEGRAM].extra["fallback_ips"] == [
+            "149.154.167.220", "149.154.167.221",
+        ]
+
+    def test_env_var_creates_platform_if_missing(self, monkeypatch):
+        from gateway.config import GatewayConfig, Platform, _apply_env_overrides
+
+        monkeypatch.setenv("TELEGRAM_FALLBACK_IPS", "149.154.167.220")
+        config = GatewayConfig(platforms={})
+        _apply_env_overrides(config)
+
+        assert Platform.TELEGRAM in config.platforms
+        assert config.platforms[Platform.TELEGRAM].extra["fallback_ips"] == ["149.154.167.220"]
+
+    def test_env_var_strips_whitespace(self, monkeypatch):
+        from gateway.config import GatewayConfig, Platform, PlatformConfig, _apply_env_overrides
+
+        monkeypatch.setenv("TELEGRAM_FALLBACK_IPS", "  149.154.167.220 , 149.154.167.221  ")
+        config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="tok")})
+        _apply_env_overrides(config)
+
+        assert config.platforms[Platform.TELEGRAM].extra["fallback_ips"] == [
+            "149.154.167.220", "149.154.167.221",
+        ]
+
+    def test_empty_env_var_does_not_populate(self, monkeypatch):
+        from gateway.config import GatewayConfig, Platform, PlatformConfig, _apply_env_overrides
+
+        monkeypatch.setenv("TELEGRAM_FALLBACK_IPS", "")
+        config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="tok")})
+        _apply_env_overrides(config)
+
+        assert "fallback_ips" not in config.platforms[Platform.TELEGRAM].extra
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# Adapter layer – _fallback_ips() reads config correctly
+# ═══════════════════════════════════════════════════════════════════════════
+
+class TestAdapterFallbackIps:
+    def _make_adapter(self, extra=None):
+        import sys
+        from unittest.mock import MagicMock
+
+        # Ensure telegram mock is in place
+        if "telegram" not in sys.modules or not hasattr(sys.modules["telegram"], "__file__"):
+            mod = MagicMock()
+            mod.ext.ContextTypes.DEFAULT_TYPE = type(None)
+            mod.constants.ParseMode.MARKDOWN_V2 = "MarkdownV2"
+            mod.constants.ChatType.GROUP = "group"
+            mod.constants.ChatType.SUPERGROUP = "supergroup"
+            mod.constants.ChatType.CHANNEL = "channel"
+            mod.constants.ChatType.PRIVATE = "private"
+            for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
+                sys.modules.setdefault(name, mod)
+
+        from gateway.config import PlatformConfig
+        from gateway.platforms.telegram import TelegramAdapter
+
+        config = PlatformConfig(enabled=True, token="test-token")
+        if extra:
+            config.extra.update(extra)
+        return TelegramAdapter(config)
+
+    def test_list_in_extra(self):
+        adapter = self._make_adapter(extra={"fallback_ips": ["149.154.167.220"]})
+        assert adapter._fallback_ips() == ["149.154.167.220"]
+
+    def test_csv_string_in_extra(self):
+        adapter = self._make_adapter(extra={"fallback_ips": "149.154.167.220,149.154.167.221"})
+        assert adapter._fallback_ips() == ["149.154.167.220", "149.154.167.221"]
+
+    def test_empty_extra(self):
+        adapter = self._make_adapter()
+        assert adapter._fallback_ips() == []
+
+    def test_no_extra_attr(self):
+        adapter = self._make_adapter()
+        adapter.config.extra = None
+        assert adapter._fallback_ips() == []
+
+    def test_invalid_ips_filtered(self):
+        adapter = self._make_adapter(extra={"fallback_ips": ["149.154.167.220", "not-valid"]})
+        assert adapter._fallback_ips() == ["149.154.167.220"]
+
+
+# ═══════════════════════════════════════════════════════════════════════════
+# DoH auto-discovery
+# ═══════════════════════════════════════════════════════════════════════════
+
+def _doh_answer(*ips: str) -> dict:
+    """Build a minimal DoH JSON response with A records."""
+    return {"Answer": [{"type": 1, "data": ip} for ip in ips]}
+
+
+class FakeDoHClient:
+    """Mock httpx.AsyncClient for DoH queries."""
+
+    def __init__(self, responses: dict):
+        # responses: URL prefix → (status, json_body) | Exception
+        self._responses = responses
+        self.requests_made: list[dict] = []
+
+    @staticmethod
+    def _make_response(status, body, url):
+        """Build an httpx.Response with a request attached (needed for raise_for_status)."""
+        request = httpx.Request("GET", url)
+        return httpx.Response(status, json=body, request=request)
+
+    async def get(self, url, *, params=None, headers=None, **kwargs):
+        self.requests_made.append({"url": url, "params": params, "headers": headers})
+        for prefix, action in self._responses.items():
+            if url.startswith(prefix):
+                if isinstance(action, Exception):
+                    raise action
+                status, body = action
+                return self._make_response(status, body, url)
+        return self._make_response(200, {}, url)
+
+    async def __aenter__(self):
+        return self
+
+    async def __aexit__(self, *args):
+        pass
+
+
+class TestDiscoverFallbackIps:
+    """Tests for discover_fallback_ips() — DoH-based auto-discovery."""
+
+    def _patch_doh(self, monkeypatch, responses, system_dns_ips=None):
+        """Wire up fake DoH client and system DNS."""
+        client = FakeDoHClient(responses)
+        monkeypatch.setattr(tnet.httpx, "AsyncClient", lambda **kw: client)
+
+        if system_dns_ips is not None:
+            addrs = [(None, None, None, None, (ip, 443)) for ip in system_dns_ips]
+            monkeypatch.setattr(tnet.socket, "getaddrinfo", lambda *a, **kw: addrs)
+        else:
+            def _fail(*a, **kw):
+                raise OSError("dns failed")
+            monkeypatch.setattr(tnet.socket, "getaddrinfo", _fail)
+        return client
+
+    @pytest.mark.asyncio
+    async def test_google_and_cloudflare_ips_collected(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.167.220")),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.167.221")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert "149.154.167.220" in ips
+        assert "149.154.167.221" in ips
+
+    @pytest.mark.asyncio
+    async def test_system_dns_ip_excluded(self, monkeypatch):
+        """The IP from system DNS is the one that doesn't work — exclude it."""
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.166.110", "149.154.167.220")),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.166.110")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == ["149.154.167.220"]
+
+    @pytest.mark.asyncio
+    async def test_doh_results_deduplicated(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.167.220")),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.167.220")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == ["149.154.167.220"]
+
+    @pytest.mark.asyncio
+    async def test_doh_timeout_falls_back_to_seed(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": httpx.TimeoutException("timeout"),
+            "https://cloudflare-dns.com": httpx.TimeoutException("timeout"),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == tnet._SEED_FALLBACK_IPS
+
+    @pytest.mark.asyncio
+    async def test_doh_connect_error_falls_back_to_seed(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": httpx.ConnectError("refused"),
+            "https://cloudflare-dns.com": httpx.ConnectError("refused"),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == tnet._SEED_FALLBACK_IPS
+
+    @pytest.mark.asyncio
+    async def test_doh_malformed_json_falls_back_to_seed(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, {"Status": 0}),  # no Answer key
+            "https://cloudflare-dns.com": (200, {"garbage": True}),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == tnet._SEED_FALLBACK_IPS
+
+    @pytest.mark.asyncio
+    async def test_one_provider_fails_other_succeeds(self, monkeypatch):
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": httpx.TimeoutException("timeout"),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.167.220")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == ["149.154.167.220"]
+
+    @pytest.mark.asyncio
+    async def test_system_dns_failure_keeps_all_doh_ips(self, monkeypatch):
+        """If system DNS fails, nothing gets excluded — all DoH IPs kept."""
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.166.110", "149.154.167.220")),
+            "https://cloudflare-dns.com": (200, _doh_answer()),
+        }, system_dns_ips=None)  # triggers OSError
+
+        ips = await tnet.discover_fallback_ips()
+        assert "149.154.166.110" in ips
+        assert "149.154.167.220" in ips
+
+    @pytest.mark.asyncio
+    async def test_all_doh_ips_same_as_system_dns_uses_seed(self, monkeypatch):
+        """DoH returns only the same blocked IP — seed list is the fallback."""
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.166.110")),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.166.110")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == tnet._SEED_FALLBACK_IPS
+
+    @pytest.mark.asyncio
+    async def test_cloudflare_gets_accept_header(self, monkeypatch):
+        client = self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, _doh_answer("149.154.167.220")),
+            "https://cloudflare-dns.com": (200, _doh_answer("149.154.167.221")),
+        }, system_dns_ips=["149.154.166.110"])
+
+        await tnet.discover_fallback_ips()
+
+        cf_reqs = [r for r in client.requests_made if "cloudflare" in r["url"]]
+        assert cf_reqs
+        assert cf_reqs[0]["headers"]["Accept"] == "application/dns-json"
+
+    @pytest.mark.asyncio
+    async def test_non_a_records_ignored(self, monkeypatch):
+        """AAAA records (type 28) and CNAME (type 5) should be skipped."""
+        answer = {
+            "Answer": [
+                {"type": 5, "data": "telegram.org"},  # CNAME
+                {"type": 28, "data": "2001:67c:4e8:f004::9"},  # AAAA
+                {"type": 1, "data": "149.154.167.220"},  # A ✓
+            ]
+        }
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, answer),
+            "https://cloudflare-dns.com": (200, _doh_answer()),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == ["149.154.167.220"]
+
+    @pytest.mark.asyncio
+    async def test_invalid_ip_in_doh_response_skipped(self, monkeypatch):
+        answer = {"Answer": [
+            {"type": 1, "data": "not-an-ip"},
+            {"type": 1, "data": "149.154.167.220"},
+        ]}
+        self._patch_doh(monkeypatch, {
+            "https://dns.google": (200, answer),
+            "https://cloudflare-dns.com": (200, _doh_answer()),
+        }, system_dns_ips=["149.154.166.110"])
+
+        ips = await tnet.discover_fallback_ips()
+        assert ips == ["149.154.167.220"]
@@ -27,7 +27,7 @@ def _ensure_telegram_mock():
    telegram_mod.constants.ChatType.CHANNEL = "channel"
    telegram_mod.constants.ChatType.PRIVATE = "private"

-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, telegram_mod)


@@ -36,6 +36,14 @@ _ensure_telegram_mock()
 from gateway.platforms.telegram import TelegramAdapter  # noqa: E402


+@pytest.fixture(autouse=True)
+def _no_auto_discovery(monkeypatch):
+    """Disable DoH auto-discovery so connect() uses the plain builder chain."""
+    async def _noop():
+        return []
+    monkeypatch.setattr("gateway.platforms.telegram.discover_fallback_ips", _noop)
+
+
 def _make_adapter() -> TelegramAdapter:
    return TelegramAdapter(PlatformConfig(enabled=True, token="test-token"))

@@ -25,7 +25,7 @@ def _ensure_telegram_mock():
    mod.constants.ChatType.SUPERGROUP = "supergroup"
    mod.constants.ChatType.CHANNEL = "channel"
    mod.constants.ChatType.PRIVATE = "private"
-    for name in ("telegram", "telegram.ext", "telegram.constants"):
+    for name in ("telegram", "telegram.ext", "telegram.constants", "telegram.request"):
        sys.modules.setdefault(name, mod)


@@ -0,0 +1,199 @@
+"""Tests for Telegram send() thread_id fallback.
+
+When message_thread_id points to a non-existent thread, Telegram returns
+BadRequest('Message thread not found'). Since BadRequest is a subclass of
+NetworkError in python-telegram-bot, the old retry loop treated this as a
+transient error and retried 3 times before silently failing — killing all
+tool progress messages, streaming responses, and typing indicators.
+
+The fix detects "thread not found" BadRequest errors and retries the send
+WITHOUT message_thread_id so the message still reaches the chat.
+"""
+
+import sys
+import types
+from types import SimpleNamespace
+
+import pytest
+
+from gateway.config import PlatformConfig, Platform
+from gateway.platforms.base import SendResult
+
+
+# ── Fake telegram.error hierarchy ──────────────────────────────────────
+# Mirrors the real python-telegram-bot hierarchy:
+#   BadRequest → NetworkError → TelegramError → Exception
+
+
+class FakeNetworkError(Exception):
+    pass
+
+
+class FakeBadRequest(FakeNetworkError):
+    pass
+
+
+# Build a fake telegram module tree so the adapter's internal imports work
+_fake_telegram = types.ModuleType("telegram")
+_fake_telegram_error = types.ModuleType("telegram.error")
+_fake_telegram_error.NetworkError = FakeNetworkError
+_fake_telegram_error.BadRequest = FakeBadRequest
+_fake_telegram.error = _fake_telegram_error
+_fake_telegram_constants = types.ModuleType("telegram.constants")
+_fake_telegram_constants.ParseMode = SimpleNamespace(MARKDOWN_V2="MarkdownV2")
+_fake_telegram.constants = _fake_telegram_constants
+
+
+@pytest.fixture(autouse=True)
+def _inject_fake_telegram(monkeypatch):
+    """Inject fake telegram modules so the adapter can import from them."""
+    monkeypatch.setitem(sys.modules, "telegram", _fake_telegram)
+    monkeypatch.setitem(sys.modules, "telegram.error", _fake_telegram_error)
+    monkeypatch.setitem(sys.modules, "telegram.constants", _fake_telegram_constants)
+
+
+def _make_adapter():
+    from gateway.platforms.telegram import TelegramAdapter
+
+    config = PlatformConfig(enabled=True, token="fake-token")
+    adapter = object.__new__(TelegramAdapter)
+    adapter._config = config
+    adapter._platform = Platform.TELEGRAM
+    adapter._connected = True
+    adapter._dm_topics = {}
+    adapter._dm_topics_config = []
+    adapter._reply_to_mode = "first"
+    adapter._fallback_ips = []
+    adapter._polling_conflict_count = 0
+    adapter._polling_network_error_count = 0
+    adapter._polling_error_callback_ref = None
+    adapter.platform = Platform.TELEGRAM
+    return adapter
+
+
+@pytest.mark.asyncio
+async def test_send_retries_without_thread_on_thread_not_found():
+    """When message_thread_id causes 'thread not found', retry without it."""
+    adapter = _make_adapter()
+
+    call_log = []
+
+    async def mock_send_message(**kwargs):
+        call_log.append(dict(kwargs))
+        tid = kwargs.get("message_thread_id")
+        if tid is not None:
+            raise FakeBadRequest("Message thread not found")
+        return SimpleNamespace(message_id=42)
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    result = await adapter.send(
+        chat_id="123",
+        content="test message",
+        metadata={"thread_id": "99999"},
+    )
+
+    assert result.success is True
+    assert result.message_id == "42"
+    # First call has thread_id, second call retries without
+    assert len(call_log) == 2
+    assert call_log[0]["message_thread_id"] == 99999
+    assert call_log[1]["message_thread_id"] is None
+
+
+@pytest.mark.asyncio
+async def test_send_raises_on_other_bad_request():
+    """Non-thread BadRequest errors should NOT be retried — they fail immediately."""
+    adapter = _make_adapter()
+
+    async def mock_send_message(**kwargs):
+        raise FakeBadRequest("Chat not found")
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    result = await adapter.send(
+        chat_id="123",
+        content="test message",
+        metadata={"thread_id": "99999"},
+    )
+
+    assert result.success is False
+    assert "Chat not found" in result.error
+
+
+@pytest.mark.asyncio
+async def test_send_without_thread_id_unaffected():
+    """Normal sends without thread_id should work as before."""
+    adapter = _make_adapter()
+
+    call_log = []
+
+    async def mock_send_message(**kwargs):
+        call_log.append(dict(kwargs))
+        return SimpleNamespace(message_id=100)
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    result = await adapter.send(
+        chat_id="123",
+        content="test message",
+    )
+
+    assert result.success is True
+    assert len(call_log) == 1
+    assert call_log[0]["message_thread_id"] is None
+
+
+@pytest.mark.asyncio
+async def test_send_retries_network_errors_normally():
+    """Real transient network errors (not BadRequest) should still be retried."""
+    adapter = _make_adapter()
+
+    attempt = [0]
+
+    async def mock_send_message(**kwargs):
+        attempt[0] += 1
+        if attempt[0] < 3:
+            raise FakeNetworkError("Connection reset")
+        return SimpleNamespace(message_id=200)
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    result = await adapter.send(
+        chat_id="123",
+        content="test message",
+    )
+
+    assert result.success is True
+    assert attempt[0] == 3  # Two retries then success
+
+
+@pytest.mark.asyncio
+async def test_thread_fallback_only_fires_once():
+    """After clearing thread_id, subsequent chunks should also use None."""
+    adapter = _make_adapter()
+
+    call_log = []
+
+    async def mock_send_message(**kwargs):
+        call_log.append(dict(kwargs))
+        tid = kwargs.get("message_thread_id")
+        if tid is not None:
+            raise FakeBadRequest("Message thread not found")
+        return SimpleNamespace(message_id=42)
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    # Send a long message that gets split into chunks
+    long_msg = "A" * 5000  # Exceeds Telegram's 4096 limit
+    result = await adapter.send(
+        chat_id="123",
+        content=long_msg,
+        metadata={"thread_id": "99999"},
+    )
+
+    assert result.success is True
+    # First chunk: attempt with thread → fail → retry without → succeed
+    # Second chunk: should use thread_id=None directly (effective_thread_id
+    # was cleared per-chunk but the metadata doesn't change between chunks)
+    # The key point: the message was delivered despite the invalid thread
@@ -0,0 +1,87 @@
+"""Tests for webhook adapter dynamic route loading."""
+
+import json
+import os
+import pytest
+from pathlib import Path
+
+from gateway.config import PlatformConfig
+from gateway.platforms.webhook import WebhookAdapter, _DYNAMIC_ROUTES_FILENAME
+
+
+def _make_adapter(routes=None, extra=None):
+    _extra = extra or {}
+    if routes:
+        _extra["routes"] = routes
+    _extra.setdefault("secret", "test-global-secret")
+    config = PlatformConfig(enabled=True, extra=_extra)
+    return WebhookAdapter(config)
+
+
+@pytest.fixture(autouse=True)
+def _isolate(tmp_path, monkeypatch):
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+
+
+class TestDynamicRouteLoading:
+    def test_no_dynamic_file(self):
+        adapter = _make_adapter(routes={"static": {"secret": "s"}})
+        adapter._reload_dynamic_routes()
+        assert "static" in adapter._routes
+        assert len(adapter._dynamic_routes) == 0
+
+    def test_loads_dynamic_routes(self, tmp_path):
+        subs = {"my-hook": {"secret": "dynamic-secret", "prompt": "test", "events": []}}
+        (tmp_path / _DYNAMIC_ROUTES_FILENAME).write_text(json.dumps(subs))
+
+        adapter = _make_adapter(routes={"static": {"secret": "s"}})
+        adapter._reload_dynamic_routes()
+        assert "my-hook" in adapter._routes
+        assert "static" in adapter._routes
+
+    def test_static_takes_precedence(self, tmp_path):
+        (tmp_path / _DYNAMIC_ROUTES_FILENAME).write_text(
+            json.dumps({"conflict": {"secret": "dynamic", "prompt": "dyn"}})
+        )
+        adapter = _make_adapter(routes={"conflict": {"secret": "static", "prompt": "stat"}})
+        adapter._reload_dynamic_routes()
+        assert adapter._routes["conflict"]["secret"] == "static"
+
+    def test_mtime_gated(self, tmp_path):
+        import time
+        path = tmp_path / _DYNAMIC_ROUTES_FILENAME
+        path.write_text(json.dumps({"v1": {"secret": "s"}}))
+
+        adapter = _make_adapter()
+        adapter._reload_dynamic_routes()
+        assert "v1" in adapter._dynamic_routes
+
+        # Same mtime — no reload
+        adapter._dynamic_routes["injected"] = True
+        adapter._reload_dynamic_routes()
+        assert "injected" in adapter._dynamic_routes
+
+        # New write — reloads
+        time.sleep(0.05)
+        path.write_text(json.dumps({"v2": {"secret": "s"}}))
+        adapter._reload_dynamic_routes()
+        assert "v2" in adapter._dynamic_routes
+        assert "v1" not in adapter._dynamic_routes
+
+    def test_file_removal_clears(self, tmp_path):
+        path = tmp_path / _DYNAMIC_ROUTES_FILENAME
+        path.write_text(json.dumps({"temp": {"secret": "s"}}))
+        adapter = _make_adapter()
+        adapter._reload_dynamic_routes()
+        assert "temp" in adapter._dynamic_routes
+
+        path.unlink()
+        adapter._reload_dynamic_routes()
+        assert len(adapter._dynamic_routes) == 0
+
+    def test_corrupted_file(self, tmp_path):
+        (tmp_path / _DYNAMIC_ROUTES_FILENAME).write_text("not json")
+        adapter = _make_adapter(routes={"static": {"secret": "s"}})
+        adapter._reload_dynamic_routes()
+        assert "static" in adapter._routes
+        assert len(adapter._dynamic_routes) == 0
@@ -105,3 +105,24 @@ class TestCmdUpdateBranchFallback:
        commands = [" ".join(str(a) for a in c.args[0]) for c in mock_run.call_args_list]
        pull_cmds = [c for c in commands if "pull" in c]
        assert len(pull_cmds) == 0
+
+    def test_update_non_interactive_skips_migration_prompt(self, mock_args, capsys):
+        """When stdin/stdout aren't TTYs, config migration prompt is skipped."""
+        with patch("shutil.which", return_value=None), patch(
+            "subprocess.run"
+        ) as mock_run, patch("builtins.input") as mock_input, patch(
+            "hermes_cli.config.get_missing_env_vars", return_value=["MISSING_KEY"]
+        ), patch("hermes_cli.config.get_missing_config_fields", return_value=[]), patch(
+            "hermes_cli.config.check_config_version", return_value=(1, 2)
+        ), patch("hermes_cli.main.sys") as mock_sys:
+            mock_sys.stdin.isatty.return_value = False
+            mock_sys.stdout.isatty.return_value = False
+            mock_run.side_effect = _make_run_side_effect(
+                branch="main", verify_ok=True, commit_count="1"
+            )
+
+            cmd_update(mock_args)
+
+            mock_input.assert_not_called()
+            captured = capsys.readouterr()
+            assert "Non-interactive session" in captured.out
@@ -1,6 +1,7 @@
 """Tests for gateway service management helpers."""

 import os
+from pathlib import Path
 from types import SimpleNamespace

 import hermes_cli.gateway as gateway_cli
@@ -152,12 +153,13 @@ class TestLaunchdServiceRecovery:
    def test_launchd_start_reloads_unloaded_job_and_retries(self, tmp_path, monkeypatch):
        plist_path = tmp_path / "ai.hermes.gateway.plist"
        plist_path.write_text(gateway_cli.generate_launchd_plist(), encoding="utf-8")
+        label = gateway_cli.get_launchd_label()

        calls = []

        def fake_run(cmd, check=False, **kwargs):
            calls.append(cmd)
-            if cmd == ["launchctl", "start", "ai.hermes.gateway"] and calls.count(cmd) == 1:
+            if cmd == ["launchctl", "start", label] and calls.count(cmd) == 1:
                raise gateway_cli.subprocess.CalledProcessError(3, cmd, stderr="Could not find service")
            return SimpleNamespace(returncode=0, stdout="", stderr="")

@@ -167,9 +169,9 @@ class TestLaunchdServiceRecovery:
        gateway_cli.launchd_start()

        assert calls == [
-            ["launchctl", "start", "ai.hermes.gateway"],
+            ["launchctl", "start", label],
            ["launchctl", "load", str(plist_path)],
-            ["launchctl", "start", "ai.hermes.gateway"],
+            ["launchctl", "start", label],
        ]

    def test_launchd_status_reports_local_stale_plist_when_unloaded(self, tmp_path, monkeypatch, capsys):
@@ -354,6 +356,20 @@ class TestGeneratedUnitUsesDetectedVenv:
        assert "/venv/" not in unit or "/.venv/" in unit


+class TestGeneratedUnitIncludesLocalBin:
+    """~/.local/bin must be in PATH so uvx/pipx tools are discoverable."""
+
+    def test_user_unit_includes_local_bin_in_path(self):
+        unit = gateway_cli.generate_systemd_unit(system=False)
+        home = str(Path.home())
+        assert f"{home}/.local/bin" in unit
+
+    def test_system_unit_includes_local_bin_in_path(self):
+        unit = gateway_cli.generate_systemd_unit(system=True)
+        # System unit uses the resolved home dir from _system_service_identity
+        assert "/.local/bin" in unit
+
+
 class TestEnsureUserSystemdEnv:
    """Tests for _ensure_user_systemd_env() D-Bus session bus auto-detection."""

@@ -94,7 +94,7 @@ class TestOfferOpenclawMigration:
        fake_mod.Migrator.assert_called_once()
        call_kwargs = fake_mod.Migrator.call_args[1]
        assert call_kwargs["execute"] is True
-        assert call_kwargs["overwrite"] is False
+        assert call_kwargs["overwrite"] is True
        assert call_kwargs["migrate_secrets"] is True
        assert call_kwargs["preset_name"] == "full"
        fake_migrator.migrate.assert_called_once()
@@ -285,3 +285,182 @@ class TestSetupWizardOpenclawIntegration:
            setup_mod.run_setup_wizard(args)

        mock_migration.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# _get_section_config_summary / _skip_configured_section — unit tests
+# ---------------------------------------------------------------------------
+
+
+class TestGetSectionConfigSummary:
+    """Test the _get_section_config_summary helper."""
+
+    def test_model_returns_none_without_api_key(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._get_section_config_summary({}, "model")
+        assert result is None
+
+    def test_model_returns_summary_with_api_key(self):
+        def env_side(key):
+            return "sk-xxx" if key == "OPENROUTER_API_KEY" else ""
+
+        with patch.object(setup_mod, "get_env_value", side_effect=env_side):
+            result = setup_mod._get_section_config_summary(
+                {"model": "openai/gpt-4"}, "model"
+            )
+        assert result == "openai/gpt-4"
+
+    def test_model_returns_dict_default_key(self):
+        def env_side(key):
+            return "sk-xxx" if key == "OPENAI_API_KEY" else ""
+
+        with patch.object(setup_mod, "get_env_value", side_effect=env_side):
+            result = setup_mod._get_section_config_summary(
+                {"model": {"default": "claude-opus-4", "provider": "anthropic"}},
+                "model",
+            )
+        assert result == "claude-opus-4"
+
+    def test_terminal_always_returns(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._get_section_config_summary(
+                {"terminal": {"backend": "docker"}}, "terminal"
+            )
+        assert result == "backend: docker"
+
+    def test_agent_always_returns(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._get_section_config_summary(
+                {"agent": {"max_turns": 120}}, "agent"
+            )
+        assert result == "max turns: 120"
+
+    def test_gateway_returns_none_without_tokens(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._get_section_config_summary({}, "gateway")
+        assert result is None
+
+    def test_gateway_lists_platforms(self):
+        def env_side(key):
+            if key == "TELEGRAM_BOT_TOKEN":
+                return "tok123"
+            if key == "DISCORD_BOT_TOKEN":
+                return "disc456"
+            return ""
+
+        with patch.object(setup_mod, "get_env_value", side_effect=env_side):
+            result = setup_mod._get_section_config_summary({}, "gateway")
+        assert "Telegram" in result
+        assert "Discord" in result
+
+    def test_tools_returns_none_without_keys(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._get_section_config_summary({}, "tools")
+        assert result is None
+
+    def test_tools_lists_configured(self):
+        def env_side(key):
+            return "key" if key == "BROWSERBASE_API_KEY" else ""
+
+        with patch.object(setup_mod, "get_env_value", side_effect=env_side):
+            result = setup_mod._get_section_config_summary({}, "tools")
+        assert "Browser" in result
+
+
+class TestSkipConfiguredSection:
+    """Test the _skip_configured_section helper."""
+
+    def test_returns_false_when_not_configured(self):
+        with patch.object(setup_mod, "get_env_value", return_value=""):
+            result = setup_mod._skip_configured_section({}, "model", "Model")
+        assert result is False
+
+    def test_returns_true_when_user_skips(self):
+        def env_side(key):
+            return "sk-xxx" if key == "OPENROUTER_API_KEY" else ""
+
+        with (
+            patch.object(setup_mod, "get_env_value", side_effect=env_side),
+            patch.object(setup_mod, "prompt_yes_no", return_value=False),
+        ):
+            result = setup_mod._skip_configured_section(
+                {"model": "openai/gpt-4"}, "model", "Model"
+            )
+        assert result is True
+
+    def test_returns_false_when_user_wants_reconfig(self):
+        def env_side(key):
+            return "sk-xxx" if key == "OPENROUTER_API_KEY" else ""
+
+        with (
+            patch.object(setup_mod, "get_env_value", side_effect=env_side),
+            patch.object(setup_mod, "prompt_yes_no", return_value=True),
+        ):
+            result = setup_mod._skip_configured_section(
+                {"model": "openai/gpt-4"}, "model", "Model"
+            )
+        assert result is False
+
+
+class TestSetupWizardSkipsConfiguredSections:
+    """After migration, already-configured sections should offer skip."""
+
+    def test_sections_skipped_when_migration_imported_settings(self, tmp_path):
+        """When migration ran and API key exists, model section should be skippable.
+
+        Simulates the real flow: get_env_value returns "" during the is_existing
+        check (before migration), then returns a key after migration imported it.
+        """
+        args = _first_time_args()
+
+        # Track whether migration has "run" — after it does, API key is available
+        migration_done = {"value": False}
+
+        def env_side(key):
+            if migration_done["value"] and key == "OPENROUTER_API_KEY":
+                return "sk-xxx"
+            return ""
+
+        def fake_migration(hermes_home):
+            migration_done["value"] = True
+            return True
+
+        reloaded_config = {"model": "openai/gpt-4"}
+
+        with (
+            patch.object(setup_mod, "ensure_hermes_home"),
+            patch.object(
+                setup_mod, "load_config",
+                side_effect=[{}, reloaded_config],
+            ),
+            patch.object(setup_mod, "get_hermes_home", return_value=tmp_path),
+            patch.object(setup_mod, "get_env_value", side_effect=env_side),
+            patch.object(setup_mod, "is_interactive_stdin", return_value=True),
+            patch("hermes_cli.auth.get_active_provider", return_value=None),
+            patch("builtins.input", return_value=""),
+            # Migration succeeds and flips the env_side flag
+            patch.object(
+                setup_mod, "_offer_openclaw_migration",
+                side_effect=fake_migration,
+            ),
+            # User says No to all reconfig prompts
+            patch.object(setup_mod, "prompt_yes_no", return_value=False),
+            patch.object(setup_mod, "setup_model_provider") as mock_model,
+            patch.object(setup_mod, "setup_terminal_backend") as mock_terminal,
+            patch.object(setup_mod, "setup_agent_settings") as mock_agent,
+            patch.object(setup_mod, "setup_gateway") as mock_gateway,
+            patch.object(setup_mod, "setup_tools") as mock_tools,
+            patch.object(setup_mod, "save_config"),
+            patch.object(setup_mod, "_print_setup_summary"),
+        ):
+            setup_mod.run_setup_wizard(args)
+
+        # Model has API key → skip offered, user said No → section NOT called
+        mock_model.assert_not_called()
+        # Terminal/agent always have a summary → skip offered, user said No
+        mock_terminal.assert_not_called()
+        mock_agent.assert_not_called()
+        # Gateway has no tokens (env_side returns "" for gateway keys) → section runs
+        mock_gateway.assert_called_once()
+        # Tools have no keys → section runs
+        mock_tools.assert_called_once()
@@ -1,10 +1,13 @@
 """
-Tests for skip_confirm behavior in /skills install and /skills uninstall.
+Tests for skip_confirm and invalidate_cache behavior in /skills install
+and /skills uninstall slash commands.

-Verifies that --yes / -y bypasses the interactive confirmation prompt
-that hangs inside prompt_toolkit's TUI.
+Slash commands always skip confirmation (input() hangs in TUI).
+Cache invalidation is deferred by default; --now opts into immediate
+invalidation (at the cost of breaking prompt cache mid-session).

 Based on PR #1595 by 333Alden333 (salvaged).
+Updated for PR #3586 (cache-aware install/uninstall).
 """

 from unittest.mock import patch, MagicMock
@@ -32,23 +35,43 @@ class TestHandleSkillsSlashInstallFlags:
            _, kwargs = mock_install.call_args
            assert kwargs.get("skip_confirm") is True

-    def test_force_flag_sets_force_not_skip(self):
+    def test_force_flag_sets_force(self):
        from hermes_cli.skills_hub import handle_skills_slash
        with patch("hermes_cli.skills_hub.do_install") as mock_install:
            handle_skills_slash("/skills install test/skill --force")
            mock_install.assert_called_once()
            _, kwargs = mock_install.call_args
            assert kwargs.get("force") is True
-            assert kwargs.get("skip_confirm") is False
+            # Slash commands always skip confirmation (input() hangs in TUI)
+            assert kwargs.get("skip_confirm") is True

-    def test_no_flags(self):
+    def test_no_flags_still_skips_confirm(self):
+        """Slash commands always skip confirmation — input() hangs in TUI."""
        from hermes_cli.skills_hub import handle_skills_slash
        with patch("hermes_cli.skills_hub.do_install") as mock_install:
            handle_skills_slash("/skills install test/skill")
            mock_install.assert_called_once()
            _, kwargs = mock_install.call_args
            assert kwargs.get("force") is False
-            assert kwargs.get("skip_confirm") is False
+            assert kwargs.get("skip_confirm") is True
+
+    def test_default_defers_cache_invalidation(self):
+        """Without --now, cache invalidation is deferred to next session."""
+        from hermes_cli.skills_hub import handle_skills_slash
+        with patch("hermes_cli.skills_hub.do_install") as mock_install:
+            handle_skills_slash("/skills install test/skill")
+            mock_install.assert_called_once()
+            _, kwargs = mock_install.call_args
+            assert kwargs.get("invalidate_cache") is False
+
+    def test_now_flag_invalidates_cache(self):
+        """--now opts into immediate cache invalidation."""
+        from hermes_cli.skills_hub import handle_skills_slash
+        with patch("hermes_cli.skills_hub.do_install") as mock_install:
+            handle_skills_slash("/skills install test/skill --now")
+            mock_install.assert_called_once()
+            _, kwargs = mock_install.call_args
+            assert kwargs.get("invalidate_cache") is True


 class TestHandleSkillsSlashUninstallFlags:
@@ -70,13 +93,32 @@ class TestHandleSkillsSlashUninstallFlags:
            _, kwargs = mock_uninstall.call_args
            assert kwargs.get("skip_confirm") is True

-    def test_no_flags(self):
+    def test_no_flags_still_skips_confirm(self):
+        """Slash commands always skip confirmation — input() hangs in TUI."""
        from hermes_cli.skills_hub import handle_skills_slash
        with patch("hermes_cli.skills_hub.do_uninstall") as mock_uninstall:
            handle_skills_slash("/skills uninstall test-skill")
            mock_uninstall.assert_called_once()
            _, kwargs = mock_uninstall.call_args
-            assert kwargs.get("skip_confirm", False) is False
+            assert kwargs.get("skip_confirm") is True
+
+    def test_default_defers_cache_invalidation(self):
+        """Without --now, cache invalidation is deferred to next session."""
+        from hermes_cli.skills_hub import handle_skills_slash
+        with patch("hermes_cli.skills_hub.do_uninstall") as mock_uninstall:
+            handle_skills_slash("/skills uninstall test-skill")
+            mock_uninstall.assert_called_once()
+            _, kwargs = mock_uninstall.call_args
+            assert kwargs.get("invalidate_cache") is False
+
+    def test_now_flag_invalidates_cache(self):
+        """--now opts into immediate cache invalidation."""
+        from hermes_cli.skills_hub import handle_skills_slash
+        with patch("hermes_cli.skills_hub.do_uninstall") as mock_uninstall:
+            handle_skills_slash("/skills uninstall test-skill --now")
+            mock_uninstall.assert_called_once()
+            _, kwargs = mock_uninstall.call_args
+            assert kwargs.get("invalidate_cache") is True


 class TestDoInstallSkipConfirm:
@@ -237,3 +237,53 @@ def test_save_platform_tools_still_preserves_mcp_with_platform_default_present()

    # Deselected configurable toolset removed
    assert "terminal" not in saved
+
+
+# ── Platform / toolset consistency ────────────────────────────────────────────
+
+
+class TestPlatformToolsetConsistency:
+    """Every platform in tools_config.PLATFORMS must have a matching toolset."""
+
+    def test_all_platforms_have_toolset_definitions(self):
+        """Each platform's default_toolset must exist in TOOLSETS."""
+        from hermes_cli.tools_config import PLATFORMS
+        from toolsets import TOOLSETS
+
+        for platform, meta in PLATFORMS.items():
+            ts_name = meta["default_toolset"]
+            assert ts_name in TOOLSETS, (
+                f"Platform {platform!r} references toolset {ts_name!r} "
+                f"which is not defined in toolsets.py"
+            )
+
+    def test_gateway_toolset_includes_all_messaging_platforms(self):
+        """hermes-gateway includes list should cover all messaging platforms."""
+        from hermes_cli.tools_config import PLATFORMS
+        from toolsets import TOOLSETS
+
+        gateway_includes = set(TOOLSETS["hermes-gateway"]["includes"])
+        # Exclude non-messaging platforms from the check
+        non_messaging = {"cli", "api_server"}
+        for platform, meta in PLATFORMS.items():
+            if platform in non_messaging:
+                continue
+            ts_name = meta["default_toolset"]
+            assert ts_name in gateway_includes, (
+                f"Platform {platform!r} toolset {ts_name!r} missing from "
+                f"hermes-gateway includes"
+            )
+
+    def test_skills_config_covers_tools_config_platforms(self):
+        """skills_config.PLATFORMS should have entries for all gateway platforms."""
+        from hermes_cli.tools_config import PLATFORMS as TOOLS_PLATFORMS
+        from hermes_cli.skills_config import PLATFORMS as SKILLS_PLATFORMS
+
+        non_messaging = {"api_server"}
+        for platform in TOOLS_PLATFORMS:
+            if platform in non_messaging:
+                continue
+            assert platform in SKILLS_PLATFORMS, (
+                f"Platform {platform!r} in tools_config but missing from "
+                f"skills_config PLATFORMS"
+            )
--- a/Show More
+++ b/Show More