Feature: suggest starting a new conversation when context degrades

Problem

As conversations grow longer, response quality degrades due to attention dilution, lost-in-the-middle effects, and context compression losses. Users have no signal that this is happening — they only notice when Claude starts giving worse answers.

Currently Claude Code compresses prior messages when approaching context limits, but this is invisible to the user. There's no proactive nudge to start a fresh conversation.

Proposal

Add a context health indicator that suggests starting a new conversation when quality is likely degrading. Possible triggers:

1. Token usage threshold — e.g., "Context is 70%+ full, consider starting a new conversation to maintain quality"
2. Compression event — when prior messages get summarized, notify the user: "Earlier messages have been compressed — some details may be lost. Consider /clear or a new session for complex tasks."
3. Turn count heuristic — after N substantive back-and-forth turns, suggest a break

Why this matters

• The degradation is gradual and invisible — users blame themselves or the model, not the conversation length
• Power users (long debugging sessions, multi-step refactors) are hit hardest and are least likely to notice mid-flow
• A simple nudge at the right time is higher value than any post-hoc fix to attention or compression

Non-goals

• This is not about increasing context window size
• Not about changing compression strategy
• Just surfacing what the system already knows (context utilization) to the user

🤖 Generated with Claude Code