Skill: strategic-compact

Trigger: "should I compact?" or "compact now?" or "context getting long" or when session is large

Description: Evaluates whether context should be compacted and guides through safe compaction that preserves all memory. Prevents the context-limit mid-task problem.

Allowed Tools: Read, Bash

When to Suggest Compaction

Suggest compacting when ANY of these are true:

• Context usage reaches 40% — hard trigger, don't wait for slowdown
• Session has 60+ back-and-forth messages
• User asks about something already resolved earlier in session
• Responses feel slow or repetitive
• A major task just completed naturally (good break point)
• Context limit warning appears

Never compact:

• Mid-task — always finish current task first
• Before saving memory to your storage system
• Before running /learn to capture session patterns

Steps

Before Compacting:

1. Capture session patterns:
   • Run /learn to extract lessons to .claude/memory/lessons.md
   • Confirm entries were written
2. Save/push memory to your storage system (GitHub, local, etc.)
3. Update STATUS.md or equivalent with current progress so it loads on resume
4. Confirm with user: "Memory saved. Safe to compact — session will resume with full context."

After Compacting:

• SessionStart hook should auto-load memory (if configured)
• Verify memory loaded by checking that project status was mentioned in first response
• If memory didn't auto-load: run your session start command manually

Notes

• Compaction is safe when memory system is properly set up — that's what it's for
• The PreCompact hook handles state preservation automatically if configured
• After compact, full project context available within 1-2 messages
• Better to compact proactively than to hit context limit mid-task