Strategic Compact Skill

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

When to Activate

Running long sessions that approach context limits (200K+ tokens)
Working on multi-phase tasks (research → plan → implement → test)
Switching between unrelated tasks within the same session
After completing a major milestone and starting new work
When responses slow down or become less coherent (context pressure)

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.js 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": "node ~/.claude/skills/strategic-compact/suggest-compact.js" }]
      },
      {
        "matcher": "Write",
        "hooks": [{ "type": "command", "command": "node ~/.claude/skills/strategic-compact/suggest-compact.js" }]
      }
    ]
  }
}

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

Token Optimization Patterns

Trigger-Table Lazy Loading

Instead of loading full skill content at session start, use a trigger table that maps keywords to skill paths. Skills load only when triggered, reducing baseline context by 50%+:

Trigger	Skill	Load When
"test", "tdd", "coverage"	tdd-workflow	User mentions testing
"security", "auth", "xss"	security-review	Security-related work
"deploy", "ci/cd"	deployment-patterns	Deployment context

Context Composition Awareness

Monitor what's consuming your context window:

CLAUDE.md files — Always loaded, keep lean
Loaded skills — Each skill adds 1-5K tokens
Conversation history — Grows with each exchange
Tool results — File reads, search results add bulk

Duplicate Instruction Detection

Common sources of duplicate context:

Same rules in both ~/.claude/rules/ and project .claude/rules/
Skills that repeat CLAUDE.md instructions
Multiple skills covering overlapping domains

Context Optimization Tools

token-optimizer MCP — Automated 95%+ token reduction via content deduplication
context-mode — Context virtualization (315KB to 5.4KB demonstrated)

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