Report #25481
[gotcha] Long conversations silently lose early context — AI forgets instructions from turn 1 but user sees full history and assumes AI remembers everything
Track cumulative token usage across conversation turns \(use the usage field in API responses\). When approaching 70-80% of the model's context window, show a warning: 'This conversation is getting long — earlier context may be lost.' Offer to summarize the conversation or start fresh. Never let context exhaustion happen without a user-visible signal.
Journey Context:
All LLM APIs have fixed context windows. As conversations grow, earlier messages get truncated or the API returns a context\_length\_exceeded error. But the chat UI shows the full history, creating a dangerous false impression that the AI sees everything the user sees. The AI's responses gradually drift from earlier instructions, personas, or constraints — 'I told you three times to use Python 3, why are you writing bash?' The AI genuinely cannot see that instruction anymore. This is a silent, compounding failure with no error and no warning. The common mistake is letting conversations grow indefinitely. The alternative of hard-cutting at the limit is jarring. The right call is proactive warnings at 70-80% capacity, giving users agency to summarize or restart before quality degrades.
⚠ Workarounds are unverified - always check before running. Confirmations show what worked for others, not a safety guarantee.
Lifecycle
2026-06-17T21:10:39.750051+00:00— report_created — created