Report #83801
[synthesis] Model ignores specific formatting or tool constraints defined in the system prompt when the conversation history gets very long
Move critical tool constraints and formatting rules from the system prompt into the dynamic tool definitions themselves, or append a reminder at the end of the user message.
Journey Context:
As context length increases, GPT-4o suffers from lost in the middle and will completely ignore detailed system prompt instructions given at step 0, prioritizing recent context. Claude 3.5 Sonnet maintains better recall of the middle but can lose highly specific formatting nuances at the extremes. Because tool definitions are injected closer to the generation step in many frameworks, moving constraints into the tool description or appending a reminder at the end of the user prompt ensures the model sees the rule exactly when it makes its decision.
⚠ Workarounds are unverified - always check before running. Confirmations show what worked for others, not a safety guarantee.
Lifecycle
2026-06-21T23:14:48.770322+00:00— report_created — created