[FEATURE] Proactive Context Management with Smart Compacting

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

Implement proactive context management to prevent workflow interruptions by warning users before reaching the
auto-compact limit and providing flexible compacting options.

Related Issues

This feature request addresses underlying causes of issues like:

• #7617: "This is constantly compacting and I cannot use it"
• #7615: "Frequent Unexpected Conversation Compaction Interrupting Workflow"

Rather than fixing the symptoms, this proposes a proactive solution that prevents disruptive auto-compacts by
giving users control and visibility.

Current Problem

• Auto-compact only triggers at 100% context capacity
• Causes abrupt interruptions during active development sessions (as reported in #7617, #7615)
• Forces immediate conversation breaks at inconvenient times
• No visibility into context usage levels
• Users lose momentum when forced to compact mid-task
• Creates frustrating "compact loops" where users can barely type before hitting limits again

Proposed Solution

1. Progressive Context Warnings

• 50% threshold: Subtle notification "Context at 50% - compact recommended when convenient"
• 70% threshold: More prominent warning "Context at 70% - consider compacting soon for optimal performance"
• 85% threshold: Urgent notice "Context at 85% - auto-compact will trigger soon"
• 95% threshold: Final warning "Auto-compact imminent - use /compact now to control timing"

1. Smart Compact Commands

• /compact --when-ready - Queues compact to trigger at next natural pause (e.g., after current task

completion)

• /compact --preview - Shows what would be preserved vs. removed before compacting
• /compact --preserve-todos - Ensures current todo lists and active work context remain intact
• /compact --threshold <percentage> - Set custom warning thresholds

1. Context Usage Visibility

• Context usage indicator: [Context: 67%] in status updates
• /context-status command to check current usage and estimated messages until auto-compact
• Optional progress bar or percentage display

1. Intelligent Auto-Compact Prevention

• Smart detection of natural break points (completed todos, finished tasks, idle periods)
• Preserve essential context (active todos, current file being worked on, recent decisions)
• Remove redundant context (old search results, completed task discussions, outdated file contents)
• Configurable auto-compact behavior - users can disable aggressive auto-compact if preferred

Benefits

• Solves #7617/#7615: Eliminates surprise interruptions and compact loops
• Improved UX: Users maintain workflow continuity
• Better Performance: Proactive management prevents performance degradation
• User Control: Flexibility to compact at convenient times
• Reduced Frustration: No more workflow-breaking surprises
• Enhanced Productivity: Developers can stay in flow state longer

Use Cases

• Long development sessions with multiple features
• Complex debugging that requires extensive context building
• Architectural discussions spanning multiple topics
• Code reviews involving many files and changes
• Any scenario currently causing issues in #7617/#7615

Implementation Considerations

• Configurable thresholds via user preferences or /config commands
• Graceful degradation if smart detection fails
• Backward compatibility with existing auto-compact behavior
• Clear user education about new features
• Address root causes of frequent compacting reported in related issues

Alternative Approaches Considered

• Simply increasing context limits (doesn't solve the core UX problem)
• Disabling auto-compact entirely (could cause performance issues)
• Only fixing the bugs in #7617/#7615 (reactive rather than proactive solution)

This feature would proactively prevent the frustrating experiences described in issues #7617 and #7615 while
significantly improving the Claude Code experience for all users, especially during long development
sessions.

Alternative Solutions

_No response_

Priority

Medium - Would be very helpful

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

_No response_