Project Session Management Skill

Track progress across work sessions using SESSION.md with git checkpoints and concrete next actions.

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When to Use

• Starting projects after project-planning generates IMPLEMENTATION_PHASES.md
• Resuming work after context clears
• Mid-phase checkpoints when context is full
• Phase transitions
• Tracking Implementation → Verification → Debugging cycle

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Phases vs Sessions

Phases (IMPLEMENTATION_PHASES.md): Units of WORK (e.g., "Database Schema", "Auth API"). Have verification/exit criteria. May span multiple sessions.

Sessions (SESSION.md): Units of CONTEXT. Complete before clearing/compacting context. Can complete a phase, part of a phase, or multiple small phases.

Example: Phase 3 (Tasks API) → Session 1 (GET/POST) → Session 2 (PATCH/DELETE) → Session 3 (verify) ✅

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Workflow

Starting New Project:

1. After project-planning creates IMPLEMENTATION_PHASES.md, offer: "Create SESSION.md to track progress?"
2. Generate SESSION.md from phases, set Phase 1 as 🔄 (in progress), set concrete "Next Action"

Ending Session:

• Automated: /wrap-session (updates SESSION.md, creates checkpoint commit, outputs summary)
• Manual: Update SESSION.md → git checkpoint → set concrete "Next Action"

Resuming:

• Automated: /continue-session (loads context, shows summary, continues from "Next Action")
• Manual: Read SESSION.md → check "Next Action" → continue

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Automation Commands

/wrap-session: Analyzes state → updates SESSION.md → updates related docs → creates checkpoint commit → outputs summary → optionally pushes

/continue-session: Loads SESSION.md + planning docs → shows git history + summary → displays verification criteria (if in Verification stage) → opens "Next Action" file → asks permission to continue

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SESSION.md Structure

Purpose: Navigation hub referencing planning docs, tracking current progress Target: <200 lines in project root Update: After significant progress (not every change)

Template

# Session State

**Current Phase**: Phase 3
**Current Stage**: Implementation (or Verification/Debugging)
**Last Checkpoint**: abc1234 (2025-10-23)
**Planning Docs**: `docs/IMPLEMENTATION_PHASES.md`, `docs/ARCHITECTURE.md`

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## Phase 1: Setup ✅
**Completed**: 2025-10-15 | **Checkpoint**: abc1234
**Summary**: Vite + React + Tailwind v4 + D1 binding

## Phase 2: Database ✅
**Completed**: 2025-10-18 | **Checkpoint**: def5678
**Summary**: D1 schema + migrations + seed data

## Phase 3: Tasks API 🔄
**Type**: API | **Started**: 2025-10-23
**Spec**: `docs/IMPLEMENTATION_PHASES.md#phase-3`

**Progress**:
- [x] GET /api/tasks endpoint (commit: ghi9012)
- [x] POST /api/tasks endpoint (commit: jkl3456)
- [ ] PATCH /api/tasks/:id ← **CURRENT**
- [ ] DELETE /api/tasks/:id
- [ ] Verify all endpoints (see IMPLEMENTATION_PHASES.md for criteria)

**Next Action**: Implement PATCH /api/tasks/:id in src/routes/tasks.ts:47, handle validation and ownership check

**Key Files**:
- `src/routes/tasks.ts`
- `src/lib/schemas.ts`

**Known Issues**: None

## Phase 4: Task UI ⏸️
**Spec**: `docs/IMPLEMENTATION_PHASES.md#phase-4`

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Status Icons

Use these emoji status icons consistently:

• ⏸️ = Not started (pending)
• 🔄 = In progress
• ✅ = Complete
• 🚫 = Blocked

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Stages Within a Phase

1. Implementation → Writing code
2. Verification → Testing against criteria
3. Debugging → Fixing issues

Update SESSION.md with current stage and progress. Example:

**Current Stage**: Verification

**Verification Progress**:
- [x] GET /api/tasks returns 200 ✅
- [x] POST /api/tasks creates task ✅
- [ ] POST with invalid data returns 400 ❌ (returns 500)

**Current Issue**: Invalid data returning 500. Check src/middleware/validate.ts

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SESSION.md Guidelines

✅ Collapse completed phases (2-3 lines), concrete "Next Action" (file+line+task), reference planning docs, checkpoint at phase end or when context full

❌ No code copying, no duplicating IMPLEMENTATION_PHASES.md, no vague actions, keep <200 lines

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Git Checkpoint Format

checkpoint: Phase [N] [Status] - [Brief Description]

Phase: [N] - [Name]
Status: [Complete/In Progress/Paused]
Session: [What was accomplished this session]

Files Changed:
- path/to/file.ts (what changed)

Next: [Concrete next action]

Example (Phase Complete):

checkpoint: Phase 3 Complete - Tasks API

Phase: 3 - Tasks API
Status: Complete
Session: Completed all CRUD endpoints and verified functionality

Files Changed:
- src/routes/tasks.ts (all CRUD operations)
- src/lib/schemas.ts (task validation)

Next: Phase 4 - Start building Task List UI component

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Expected Uncommitted Files (CRITICAL)

Checkpoint Cycle: /wrap-session creates commit → gets hash → updates SESSION.md with hash. Therefore SESSION.md is always uncommitted when resuming (BY DESIGN).

Expected uncommitted files (no warning):

• SESSION.md - Checkpoint hash updated post-commit, always uncommitted between sessions (NORMAL)
• CLAUDE.md - Often updated during dev, may be uncommitted (NORMAL)
• .roomodes - Editor/IDE state, not relevant to session handoff (SAFE TO IGNORE)

Warning triggers (unexpected):

• Source files (.ts, .tsx, .js)
• Config files (vite.config.ts, wrangler.jsonc)
• Planning docs (IMPLEMENTATION_PHASES.md, ARCHITECTURE.md)
• New untracked files

/continue-session behavior:

• ℹ️ Info message when only SESSION.md/CLAUDE.md/.roomodes uncommitted
• ⚠️ Warning when code/doc changes uncommitted (shows filtered list excluding expected files)

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Context Management

Context full mid-phase: Update SESSION.md → checkpoint → clear context → read SESSION.md + planning docs → continue from "Next Action"

Phase complete: Check verification criteria → mark 🔄→✅ → checkpoint → move next phase ⏸️→🔄

Troubleshooting: Update to "Debugging" stage → document "Current Issue" → when fixed, return to "Verification" or "Implementation"

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Integration with project-planning

project-planning generates IMPLEMENTATION_PHASES.md (the plan) → project-session-management creates SESSION.md (the tracker) → work through phases → git checkpoints → resume from SESSION.md

Planning docs (/docs): Reference material, rarely change SESSION.md (root): Living document, updates constantly

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Creating SESSION.md for New Project

After project-planning runs:

1. Read IMPLEMENTATION_PHASES.md
2. Create SESSION.md in root: Phase 1 as 🔄, others as ⏸️
3. Expand Phase 1 with task checklist
4. Set concrete "Next Action"
5. Output for review

Offer: "Would you like me to create SESSION.md to track progress through these phases? (clear current phase, progress tracking, easy resume, git checkpoint format)"

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Bundled Resources

Templates: SESSION.md.template, checkpoint-commit-format.md, CLAUDE-session-snippet.md

Scripts: resume.sh (show current state)

References: session-handoff-protocol.md, best-practices.md