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strategic-compact

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Strategic Compact

Intelligent context management that suggests compaction at optimal moments.

Core Principle

Manual compaction at strategic points > Auto-compaction at arbitrary points

Auto-compact triggers at context limits, often mid-task. Strategic compaction preserves context through logical phases and compacts at natural transition points.

When to Suggest Compaction

Optimal Compaction Points

TriggerReason
Exploration complete, implementation startingExploration context rarely needed for coding
Milestone completedClean slate for next phase
Plan finalized and documentedPlan captured, context can reset
Debug session resolvedDebug traces clutter future work
Switching to unrelated taskPrevious context not relevant
50+ tool calls in sessionAccumulated context likely stale

Avoid Compaction During

ScenarioWhy
Mid-implementationLoses code context and decisions
Active debuggingLoses diagnostic information
Incomplete taskMay need earlier context
Code review in progressLoses review thread

Compaction Options

/compact (Quick)

  • Built-in summarization
  • Frees context immediately
  • May lose some nuance

/handoff (Recommended for complex work)

Creates HANDOFF.md with:

  • Current goal and progress
  • What worked / what didn't
  • Next steps
  • Key decisions made

Then start fresh with: > HANDOFF.md

/clear (Fresh start)

  • Complete reset
  • Best when switching tasks entirely

Phase Detection Patterns

Detect phase transitions by monitoring:

EXPLORATION → IMPLEMENTATION
- Many Read/Grep/Glob calls → Edit/Write calls starting
- Questions answered → Code being written

IMPLEMENTATION → TESTING
- Edit/Write heavy → Bash(test) calls
- Feature code done → Verification starting

DEBUGGING → RESOLUTION
- Error investigation → Fix confirmed working
- Multiple attempts → Success achieved

Automatic Behavior

This skill works with hooks that:

  1. Track tool usage - Counts tool calls per session
  2. Detect phase transitions - Monitors tool patterns
  3. Inject suggestions - Adds context-aware recommendations

Usage Patterns

After Exploration

[Hook detects: 30+ Read/Grep calls, first Edit coming]
→ Suggest: "Exploration complete. Consider /compact before implementation."

After Milestone

[Hook detects: Tests passing after implementation]
→ Suggest: "Milestone reached. Good time for /compact or /handoff."

Context Threshold

[Hook detects: 50 tool calls reached]
→ Suggest: "Session has 50+ tool calls. Consider /compact if context feels stale."

Integration

Works automatically via plugin hooks. No manual configuration needed.

The hooks:

  • Run on PreToolUse to track and suggest
  • Run on PreCompact to add custom instructions
  • Provide non-blocking suggestions via stderr

Source

git clone https://github.com/anilcancakir/claude-code-plugins/blob/main/strategic-compact/skills/strategic-compact/SKILL.mdView on GitHub

Overview

Strategic Compact provides intelligent guidance on when to compact context during Claude Code sessions. It activates on context pressure, detected phase transitions, or user prompts like 'running out of context' or 'conversation too long', steering you toward deliberate, phase-aware compaction.

How This Skill Works

It monitors tool usage and phase transitions by analyzing patterns (e.g., Read/Grep/Glob vs Edit/Write, test calls) and then injects non-blocking suggestions. You then perform the chosen action (/compact, /handoff, or /clear) to reset or preserve context. A HANDOFF.md is created when using /handoff and you start fresh.

When to Use It

  • Exploration complete, implementation starting
  • Milestone completed
  • Plan finalized and documented
  • Debug session resolved
  • Switching to unrelated task

Quick Start

  1. Step 1: Ensure the Strategic Compact skill is active (auto via hooks).
  2. Step 2: Work and watch for phase-transition cues or long-context prompts.
  3. Step 3: When prompted, choose /compact, /handoff, or /clear; then start the next phase.

Best Practices

  • Aim for compaction at clear phase boundaries rather than mid-task
  • Use /handoff for complex work to preserve decisions and context
  • Avoid compaction during mid-implementation or active debugging
  • Document plan and progress before compacting and review HANDOFF.md
  • Reset context with /clear when starting a wholly new task

Example Use Cases

  • Exploration complete triggers a suggestion to compact before implementation
  • Milestone reached; /handoff captures progress and next steps
  • Context grows past 50 tool calls; compact to reduce drift
  • Debug session resolves; compact to clear diagnostic clutter
  • Switching to an unrelated task; clear context and start fresh

Frequently Asked Questions

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