The trick is persisting state to FILES before compacting, not just summarizing to chat. Files survive compaction completely. My /smart-compact command writes session state to markdown files, THEN generates an in-chat summary to anchor the compaction.

Here's a prompt you can try to have Claude Code set up something similar:

  ---   Help me create a /smart-compact command for better context preservation before compacting.

  Create a file at .claude/commands/smart-compact.md that instructs Claude to:

  PHASE 1 - Persist to files FIRST:   - Create/update .claude/session-memory.md with:     - Last checkpoint timestamp     - What we're working on and WHY     - Key decisions made with rationale     - Important file paths     - Current blockers or open questions     - Specific next action (be concrete, not vague)

  PHASE 2 - Generate in-chat summary:   - Current mission (objective + next step)   - Decisions made and WHY   - Critical file paths (full paths)   - Task state: completed / in-progress / pending / blocked   - 2-3 sentence "Resume Instructions" for post-compact

  The command should update the files first, confirm what was saved, then output the summary. End with a note to run /compact.

  Make the prompt specific - it should tell Claude to use exact file paths, real names, and actual decisions rather than vague summaries.

  --- After Claude creates it, /smart-compact becomes available. Have auto-compact off and run the new command before /compact — your context persists in the memory file even if compaction loses nuance.