strategic-compact

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:

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

Hook Setup

Installed as a plugin? No setup is needed. The plugin's hooks/hooks.json already registers suggest-compact.js (hook id pre:edit-write:suggest-compact, active in the standard and strict hook profiles). Do not copy the block below into ~/.claude/settings.json — ~/.claude/scripts/ does not exist on plugin installs, and duplicating a plugin hook causes double execution.

If installed manually (./install.sh), add to your ~/.claude/settings.json:

{
  "hooks": {
    "PreToolUse": [
      {
        "matcher": "Edit",
        "hooks": [{ "type": "command", "command": "node ~/.claude/scripts/hooks/suggest-compact.js" }]
      },
      {
        "matcher": "Write",
        "hooks": [{ "type": "command", "command": "node ~/.claude/scripts/hooks/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 written down (a file, or the task list if you have one); 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 |

| Files on disk | File contents you previously read |

| Memory files (~/.claude/memory/) | Multi-step conversation context |

| Git state (commits, branches) | Tool call history and counts |

| The task list — only if you have the todo tools (see below) | Nuanced user preferences stated verbally |

> ### Don't rely on the task list surviving — it may not exist

>

> Claude Code 2.1.233 removed the todo/task tools by default on Opus 4.8, Sonnet 5,

> Fable 5, Mythos 5 and newer models (TodoWrite, TaskCreate/Get/Update/List).

> CLAUDE_CODE_ENABLE_TODO_TOOLS=1 brings them back, but that is a per-machine

> environment setting — it does not travel with this skill, so you cannot assume the

> reader has it.

>

> This matters because "my todo list survives compaction" is a reason people compact

> instead of writing state down. If the tools are absent there is no list to survive,

> and the plan is simply gone. Write the plan to a file before compacting — a file

> persists on every version and every model. Treat the task list as a convenience that

> may be missing, never as your durable record.

Best Practices

1. Compact after planning — Once the plan is finalized and written to a file, compact to start fresh
2. Compact after debugging — Clear error-resolution context before continuing
3. Don't compact mid-implementation — Preserve context for related changes
4. Read the suggestion — The hook tells you when, you decide if
5. Write before compacting — Save important context to files or memory before compacting
6. 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)

Related

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