Strategic Compact

Strategic Compact

Save current session state before context window compaction so critical context is not lost.

When to Use

• Before running /compact
• When conversation is getting long (100+ messages)
• Before switching to a complex new task mid-session
• When you want to preserve decisions and progress

Algorithm

1. Gather session state by scanning the current conversation for:

   • Decisions made (architectural choices, trade-offs, rejected alternatives)
   • Files modified or created (with brief description of changes)
   • Current task and its status (in-progress, blocked, completed)
   • Next steps planned but not yet executed
   • Key findings (bugs found, patterns discovered, constraints identified)
   • Open questions or blockers

2. Ensure target directory exists:

   ~/.claude/sessions/
   

3. Write checkpoint file to ~/.claude/sessions/checkpoint_{YYYY-MM-DD}_{HHMM}.md with this structure:

   # Session Checkpoint - {date} {time}
   
   ## Current Task
   {What we're working on and current status}
   
   ## Decisions Made
   - {decision 1}: {rationale}
   - {decision 2}: {rationale}
   
   ## Files Modified
   - `{path}`: {what changed and why}
   
   ## Key Findings
   - {finding 1}
   - {finding 2}
   
   ## Next Steps
   1. {next action 1}
   2. {next action 2}
   
   ## Open Questions
   - {question or blocker}
   

4. Confirm to user with file path and summary of what was saved.

5. Post-compaction reload: After compaction, user can ask to read the checkpoint file to restore context.

Notes

• Keep checkpoint concise: max 100 lines to avoid bloating future context
• One checkpoint per save (overwrite if same minute, otherwise new file)
• Suggest compaction when conversation feels slow or repetitive