Strategic Compact Skill Skill

Strategic Compact Skill

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

Maestro Integration

Lifecycle: design Activates when: maestro:new-track detects relevant tech in tech-stack.md, or maestro:implement encounters matching task types.

Phase Guidance

In maestro:design: Suggest compaction between major phases (research to plan, plan to implement). Preserve critical decisions across compaction boundaries.

Related Skills

maestro:iterative-retrieval
maestro:autonomous-loops
maestro:continuous-learning

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": "Edit",
        "hooks": [{ "type": "command", "command": "bash ~/.claude/skills/maestro:strategic-compact/suggest-compact.sh" }]
      },
      {
        "matcher": "Write",
        "hooks": [{ "type": "command", "command": "bash ~/.claude/skills/maestro:strategic-compact/suggest-compact.sh" }]
      }
    ]
  }
}

Configuration

Environment variables:

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

Compaction Decision Guide

Use this table to decide when to compact:

| Phase Transition | Compact? | Why | |-----------------|----------|-----| | Research → Planning | Yes | Research context is bulky; plan is the distilled output | | Planning → Implementation | Yes | Plan is in TodoWrite or a file; free up context for code | | Implementation → Testing | Maybe | Keep if tests reference recent code; compact if switching focus | | Debugging → Next feature | Yes | Debug traces pollute context for unrelated work | | Mid-implementation | No | Losing variable names, file paths, and partial state is costly | | After a failed approach | Yes | Clear the dead-end reasoning before trying a new approach |

What Survives Compaction

Understanding what persists helps you compact with confidence:

| Persists | Lost | |----------|------| | CLAUDE.md instructions | Intermediate reasoning and analysis | | TodoWrite task list | File contents you previously read | | Memory files (~/.claude/memory/) | Multi-step conversation context | | Git state (commits, branches) | Tool call history and counts | | Files on disk | Nuanced user preferences stated verbally |

Best Practices

Compact after planning — Once plan is finalized in TodoWrite, 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
Write before compacting — Save important context to files or memory before compacting
Use /compact with a summary — Add a custom message: /compact Focus on implementing auth middleware next

The Longform Guide — Token optimization section
Memory persistence hooks — For state that survives compaction
continuous-learning skill — Extracts patterns before session ends

Relationship to Maestro Workflow

/maestro:new-track -- Detects this skill during Step 9.5 (skill matching)
/maestro:implement -- Loads this skill's guidance during task execution
/maestro:review -- Uses checklists as review criteria

Agent Skills: Strategic Compact Skill

Install this agent skill to your local

Skill Files