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

Trigger	Reason
Exploration complete, implementation starting	Exploration context rarely needed for coding
Milestone completed	Clean slate for next phase
Plan finalized and documented	Plan captured, context can reset
Debug session resolved	Debug traces clutter future work
Switching to unrelated task	Previous context not relevant
50+ tool calls in session	Accumulated context likely stale

Avoid Compaction During

Scenario	Why
Mid-implementation	Loses code context and decisions
Active debugging	Loses diagnostic information
Incomplete task	May need earlier context
Code review in progress	Loses 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:

code

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:

•Track tool usage - Counts tool calls per session
•Detect phase transitions - Monitors tool patterns
•Inject suggestions - Adds context-aware recommendations

Usage Patterns

After Exploration

code

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

After Milestone

code

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

Context Threshold

code

[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