Project Session Management Skill
Track progress across work sessions using SESSION.md with git checkpoints and concrete next actions.
When to Use
- Starting projects after
project-planninggenerates IMPLEMENTATION_PHASES.md - Resuming work after context clears
- Mid-phase checkpoints when context is full
- Phase transitions
- Tracking Implementation → Verification → Debugging cycle
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) ✅
Workflow
Starting New Project:
- After
project-planningcreates IMPLEMENTATION_PHASES.md, offer: "Create SESSION.md to track progress?" - 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
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
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`
---
## 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`Status Icons
Use these emoji status icons consistently:
- ⏸️ = Not started (pending)
- 🔄 = In progress
- ✅ = Complete
- 🚫 = Blocked
Stages Within a Phase
- Implementation → Writing code
- Verification → Testing against criteria
- 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.tsSESSION.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
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 componentExpected 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)
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"
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
Creating SESSION.md for New Project
After project-planning runs:
- Read IMPLEMENTATION_PHASES.md
- Create SESSION.md in root: Phase 1 as 🔄, others as ⏸️
- Expand Phase 1 with task checklist
- Set concrete "Next Action"
- 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)"
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