Feature Request: Context Management Options (--compress-record, --context-mode)

Summary

Add CLI flags and configuration options for users to control context window management behavior, specifically around compression/purging and automatic session record creation.

Problem

When context compression or purging occurs, valuable session information is lost permanently. Users have no way to:

1. Automatically preserve session details before compression
2. Choose between compression (summarization) vs full purge
3. Ensure continuity across long sessions

Proposed Solution

1. --compress-record / --comprec

Automatically create a comprehensive session record file before context compression occurs.

claude --comprec                    # Enable for this session
claude --compress-record=auto       # Auto-create when context < 10%
claude --compress-record=prompt     # Prompt user before compression
claude --compress-record=off        # Default current behavior

Behavior:

• When context window reaches threshold (configurable, default 5-10%), automatically:

1. Generate SESSION_RECORD_YYYY-MM-DD-HHMMSS.md in current project
2. Include: all tasks, files modified, commits, decisions, errors, pending work
3. Then proceed with compression

2. --context-mode

Let users choose between compression and full purge.

claude --context-mode=compress      # Default: summarize and continue
claude --context-mode=purge         # Full clear, start fresh
claude --context-mode=checkpoint    # Save record, then purge

Use cases:

• compress (default): Long-running sessions where continuity matters
• purge: When context has become cluttered/confused, start fresh
• checkpoint: Best of both - save everything, then clean slate

3. Configuration File Support

{
  "context": {
    "compress_record": true,
    "record_threshold_percent": 8,
    "record_location": "docs/session-records/",
    "mode": "compress"
  }
}

Session Record Format Example

# Session Record: [Project] - YYYY-MM-DD HH:MM

## Summary
[Auto-generated summary of session goals and outcomes]

## Tasks Completed
- [x] Task 1
- [ ] Task 2 (pending)

## Files Modified
| File | Action | Commit |
|------|--------|--------|
| src/main.cpp | Modified | abc1234 |

## Commits Made
- `abc1234` - commit message

## Key Decisions
- Decision 1: chose X over Y because...

## Pending Work
- Item 1

## Context for Next Session
[What the next session needs to know]

Benefits

1. No information loss: Compression/purging currently loses details permanently
2. Auditability: Users can review exactly what Claude did in a session
3. Continuity: Easy to resume work even after full context reset
4. Collaboration: Session records can be shared with team members
5. Debugging: When something goes wrong, the record shows what happened
6. User control: Choice between compression behaviors based on workflow needs

Privacy Considerations

• Session records may contain sensitive info
• Default: add SESSION_RECORD*.md to .gitignore
• Option: --compress-record=sanitized to strip sensitive patterns

Current Workaround

Users can manually create session records before compression, but this is easy to forget and not integrated with context management.