progress-sync

name	progress-sync
description	Auto-sync plan checkboxes across agents and sessions. Crash-resilient progress tracking that survives IDE crashes and terminal closes. Use when working on plans, after completing tasks, or resuming work.
version	2.0.0
triggers	["**/plans/**/*.md","**/plan.md","**/phase-*.md"]

Progress Sync - Crash-Resilient Progress Tracking

Never lose progress again. This skill ensures plan checkboxes are always updated when work completes, whether by main agent, subagents, or teams.

Core Principle

Checkboxes in plan files ARE the source of truth. Memory bank augments but doesn't replace.

How It Works

1. Checkpoint Markers (Required in Plans)

Plans must use checkpoint markers for reliable parsing:

## Phase 1: Setup
<!-- CHECKPOINT: phase-1-setup -->

### Tasks
- [ ] Create database schema <!-- TASK: db-schema -->
- [ ] Setup auth middleware <!-- TASK: auth-middleware -->
- [x] Configure environment <!-- TASK: env-config -->

### Acceptance Criteria
- [ ] All migrations pass <!-- ACCEPT: migrations -->
- [ ] Tests green <!-- ACCEPT: tests -->

2. Auto-Sync Triggers

Progress syncs automatically on:

• PostToolUse: Edit/Write on plan files → parse checkboxes → update memory
• SubagentStop: Any agent completes → update parent plan checkboxes
• SessionStart: Load checkpoint, show what's done/pending
• UserPromptSubmit: After 5+ tool calls → checkpoint

3. Checkpoint File Structure

plans/260220-1149-feature/
├── plan.md                    # Source of truth (checkboxes here)
├── .checkpoint/
│   ├── state.json            # Current progress snapshot
│   ├── history.jsonl         # Append-only activity log
│   └── recovery.json         # Last known good state
└── phase-01-*.md             # Phase files (also tracked)

4. state.json Schema

{
  "version": 2,
  "planId": "260220-1149-feature",
  "lastCheckpoint": "2026-02-20T11:49:00Z",
  "checksum": "sha256:abc123",
  "progress": {
    "totalTasks": 15,
    "completedTasks": 7,
    "percentage": 46.7
  },
  "phases": {
    "phase-1-setup": {
      "status": "completed",
      "tasks": {
        "db-schema": { "done": true, "completedAt": "...", "completedBy": "main" },
        "auth-middleware": { "done": true, "completedAt": "...", "completedBy": "subagent:fullstack" },
        "env-config": { "done": true, "completedAt": "...", "completedBy": "main" }
      }
    },
    "phase-2-core": {
      "status": "in_progress",
      "tasks": {...}
    }
  },
  "currentPhase": "phase-2-core",
  "currentTask": "user-endpoints",
  "blockers": [],
  "decisions": [
    { "time": "...", "decision": "Using async SQLAlchemy 2.0", "reason": "Better performance" }
  ],
  "sessionNotes": "API structure complete, working on user management"
}

Commands

Manual Checkpoint

/progress:save [notes]

Force checkpoint with optional notes.

View Progress

/progress:status

Show current progress with visual indicators:

[Progress Sync] Plan: 260220-1149-feature
━━━━━━━━━━━━━━━━━━━━ 47% (7/15 tasks)

Phase 1: Setup ✓ COMPLETE
  [x] db-schema (main, 2h ago)
  [x] auth-middleware (fullstack-agent, 1h ago)
  [x] env-config (main, 3h ago)

Phase 2: Core API ◐ IN PROGRESS
  [x] health-endpoint (main, 30m ago)
  [ ] user-endpoints ← CURRENT
  [ ] role-permissions
  [ ] api-validation

Next: user-endpoints
Notes: "API structure complete, working on user management"

Recover from Crash

/progress:recover

Restore from last known good state if plan.md is corrupted.

Sync from Plan (Re-parse)

/progress:parse

Re-read plan.md and rebuild checkpoint state from checkboxes.

Subagent Protocol

When spawning subagents, include checkpoint context:

Task: "Implement user authentication"

[CHECKPOINT CONTEXT]
Plan: /path/to/plans/260220-1149-feature/plan.md
Phase: phase-2-core
Tasks to complete:
- [ ] auth-middleware <!-- TASK: auth-middleware -->
- [ ] session-handling <!-- TASK: session-handling -->

On completion, update checkboxes in plan.md directly.
Mark: `- [x] task name <!-- TASK: id -->`

Subagent Completion Hook

Subagents MUST update plan.md checkboxes before returning:

// In subagent final report:
"I have completed the following tasks and updated plan.md:
- [x] auth-middleware
- [x] session-handling"

The progress-sync-hook.cjs will:

1. Detect SubagentStop event
2. Parse subagent output for completed tasks
3. Update state.json checkpoint
4. Verify plan.md checkboxes match

Integration with Existing Memory Bank

Progress Sync REPLACES the old memory-bank skill for plan tracking:

Old (memory-bank)	New (progress-sync)
.memory/progress.json	.checkpoint/state.json
Manual save via command	Auto-save on triggers
No checkbox sync	Checkbox sync core feature
History in same file	Append-only history.jsonl
No crash recovery	recovery.json backup

Best Practices

For Plan Authors

1. Use checkpoint markers - Add <!-- CHECKPOINT: id --> to phases
2. Use task markers - Add <!-- TASK: id --> to checkboxes
3. Keep tasks atomic - One checkbox = one deliverable
4. Group by phase - Phases have clear boundaries

For Main Agent

1. Check progress first - Run /progress:status when resuming
2. Include checkpoint context in subagent prompts
3. Verify after subagents - Check checkboxes were updated
4. Save notes before stopping - /progress:save "stopped at user validation"

For Subagents

1. Update plan.md directly when completing tasks
2. Report what was completed in final message
3. Don't modify unassigned tasks - Only check off YOUR work

Crash Recovery Flow

When session starts after crash:

1. Hook reads .checkpoint/state.json
2. Compares with plan.md checkboxes
3. If mismatch → parse plan.md as source of truth
4. If plan.md corrupted → restore from recovery.json
5. Output resume context to Claude

[Progress Sync] Recovered from crash
  Last checkpoint: 15m ago
  Recovered state: 7/15 tasks complete
  Current phase: phase-2-core
  Resume from: user-endpoints

Limitations

• Requires checkpoint markers for reliable tracking
• Large plans (100+ tasks) may slow parsing
• Nested subagents (3+ levels) may miss updates
• Team agents need explicit coordination

Migration from memory-bank

Existing .memory/ folders continue working. To migrate:

1. Add checkpoint markers to existing plans
2. Run /progress:parse to initialize .checkpoint/
3. Old memory-bank hooks will be deprecated

Files

• SKILL.md - This documentation
• references/checkpoint-format.md - Detailed schema docs
• references/subagent-protocol.md - Multi-agent coordination