[FEATURE] Add context window usage indicator and warning before auto-compaction
Preflight Checklist
- [x] I have searched existing requests and this feature hasn't been requested yet
- [x] This is a single feature request (not multiple features)
Problem Statement
When a session's context window approaches its limit, Claude Code silently triggers
auto-compaction with no prior warning to the user. From the user's perspective,
the conversation history simply disappears — with no countdown, no icon, no alert.
This is especially disruptive for long, multi-step project sessions where losing
context mid-work causes real productivity loss and confusion.
Proposed Solution
Expected Behavior
- A visible indicator (progress bar, icon, or badge) showing current context usage
- A warning notification when context is near saturation (e.g., at 70–80%)
- Optional: prompt the user to save a handoff note or summary before compaction occurs
Current Behavior
No indicator or warning exists. Auto-compaction happens silently.
Why This Matters
Claude Web retains conversation history across sessions. Users migrating from
Claude Web to the desktop app expect similar reliability. Silent context loss
without warning breaks trust and discourages long-term project use.
Alternative Solutions
_No response_
Priority
Critical - Blocking my work
Feature Category
CLI commands and flags
Use Case Example
_No response_
Additional Context
_No response_
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