Strategic Compact Skill

Suggests manual /compact at strategic points in your workflow rather than relying on arbitrary auto-compaction.

Why Strategic Compaction?

Auto-compaction triggers at arbitrary points:

Often mid-task, losing important context
No awareness of logical task boundaries
Can interrupt complex multi-step operations

Strategic compaction at logical boundaries:

After exploration, before execution - Compact research context, keep implementation plan
After completing a milestone - Fresh start for next phase
Before major context shifts - Clear exploration context before different task

How It Works

The suggest-compact.sh script runs on PreToolUse (Edit/Write) and:

Tracks tool calls - Counts tool invocations in session
Threshold detection - Suggests at configurable threshold (default: 50 calls)
Periodic reminders - Reminds every 25 calls after threshold

Hook Setup

Add to your ~/.claude/settings.json:

{
  "hooks": {
    "PreToolUse": [{
      "matcher": "tool == \"Edit\" || tool == \"Write\"",
      "hooks": [{
        "type": "command",
        "command": "~/.claude/skills/strategic-compact/suggest-compact.sh"
      }]
    }]
  }
}

Configuration

Environment variables:

COMPACT_THRESHOLD - Tool calls before first suggestion (default: 50)

Best Practices

Compact after planning - Once plan is finalized, compact to start fresh
Compact after debugging - Clear error-resolution context before continuing
Don't compact mid-implementation - Preserve context for related changes
Read the suggestion - The hook tells you when, you decide if

The Longform Guide - Token optimization section
Memory persistence hooks - For state that survives compaction

strategic-compact