When a gateway session exceeds the model's context window, Anthropic may
return a generic 400 invalid_request_error with just 'Error' as the
message. This bypassed the phrase-based context-length detection,
causing the agent to treat it as a non-retryable client error. Worse,
the failed user message was still persisted to the transcript, making
the session even larger on each attempt — creating an infinite loop.
Three-layer fix:
1. run_agent.py — Fallback heuristic: when a 400 error has a very short
generic message AND the session is large (>40% of context or >80
messages), treat it as a probable context overflow and trigger
compression instead of aborting.
2. run_agent.py + gateway/run.py — Don't persist failed messages:
when the agent returns failed=True before generating any response,
skip writing the user's message to the transcript/DB. This prevents
the session from growing on each failure.
3. gateway/run.py — Smarter error messages: detect context-overflow
failures and suggest /compact or /reset specifically, instead of a
generic 'try again' that will fail identically.
teknium1
75a2b77b0d