Session Continuity and Strategic Compaction

Long sessions typically suffer from two issues:

• Context gets muddy: the longer you go, the more constraints get lost and drift increases.
• After an interruption, you can’t restart cleanly: you have to re-explain the background the next day.

Treat this as an engineering problem: use Hooks to create traceable checkpoints, and make compaction (compact) a deliberate choice rather than a random automatic event.

1) Strategic compaction: use compact at phase boundaries

Instead of waiting for auto-compaction to trigger at a random time, compact at points you control:

• after exploration/research, before you start editing
• after a milestone (a module is done and tests are green), before moving to the next
• when context is near full and the model starts forgetting/drifting (check /context first)

If your version supports /compact (or similar), treat it as a “phase transition” ritual.

2) Hook “pre-compaction markers”: PreCompact

A practical idea: on PreCompact, log “a compaction happened”, so later you can understand discontinuities in the record.

One implementation writes to ~/.claude/sessions/compaction-log.txt and appends a marker to the most recent session file:

• hooks/memory-persistence/pre-compact.sh

The goal is not to copy scripts verbatim, but to make compaction explicit and traceable.

3) Session handoff via Hooks: SessionStart / SessionEnd

The pattern: at session end, write a daily handoff file (example ~/.claude/sessions/YYYY-MM-DD-session.tmp) containing:

• current status (where you are)
• done/in-progress lists
• next minimal action
• which context files to load next time

If you don’t want scripts, you can maintain a SCRATCH.md or SESSION.md manually. Template:

## Task headline (one sentence)

## Done
- ...

## Not done
- ...

## Next minimal action (executable)
- ...

## Verification (commands/pages/logs)
- ...

## Files to load next time
- `path/to/file`

4) Start with reminder Hooks, not blocking Hooks

Repos often use both reminder-style hooks (suggest tmux for long commands) and blocking hooks (exit 1 to forbid risky actions). Team rollout advice:

1. start with reminders (low friction)
2. add validation hooks (console.log scans, format/typecheck)
3. only then consider blockers (and document “why/how to bypass/who maintains it”)

5) A subtle footgun: counters must use a stable key

One script idea is “suggest compact after N tool calls” (hooks/strategic-compact/suggest-compact.sh). Watch out: if you use $$ in temp file names, each run gets a different counter file, so the count never accumulates.

If you want accumulated reminders, use a stable key (fixed filename, or a stable session ID env var if your version provides one).

Next steps

• learn hook events and config: see Hooks
• operationalize a minimal team setup: start from Team Starter Kit

Reference

• Related pages on this site:
  • Hooks