Session Management Skill

For maintaining context across long development sessions and enabling seamless resume after breaks.

Core Principle

Checkpoint at natural breakpoints, resume instantly.

Long development sessions risk context loss. Proactively document state, decisions, and progress so any session can resume exactly where it left off - whether returning after a break or hitting context limits.

Tiered Summarization Rules

Tier 1: Quick Update (current-state.md only)

Trigger: After completing any small task or todo item Action: Update "Active Task", "Progress", and "Next Steps" sections Time: ~30 seconds

Tier 2: Full Checkpoint (current-state.md + decisions.md)

Trigger:

• After completing a feature or significant change
• After any architectural/library decision
• After ~20 tool calls during active work
• When switching to a different area of the codebase

Action:

1. Update full current-state.md
2. Log any decisions to decisions.md
3. Update files being modified table

Tier 3: Session Archive (archive/ + full checkpoint)

Trigger:

• End of work session
• Completing a major feature/milestone
• Before a significant context shift
• When context feels heavy (~50+ tool calls)

Action:

1. Create archive entry: archive/YYYY-MM-DD[-topic].md
2. Full checkpoint
3. Clear verbose notes from current-state.md
4. Update code-landmarks.md if new patterns introduced

Decision Heuristic

┌─────────────────────────────────────────────────────┐
│ After completing work, ask:                         │
├─────────────────────────────────────────────────────┤
│ Was a decision made?        → Log to decisions.md   │
│ Task took >10 tool calls?   → Full Checkpoint       │
│ Major feature complete?     → Archive               │
│ Ending session?             → Archive + Handoff     │
│ Otherwise                   → Quick Update          │
└─────────────────────────────────────────────────────┘

Session State Structure

Create _project_specs/session/ directory:

_project_specs/
└── session/
    ├── current-state.md      # Live session state (update frequently)
    ├── decisions.md          # Key decisions log (append-only)
    ├── code-landmarks.md     # Important code locations
    └── archive/              # Past session summaries
        └── 2025-01-15.md

Current State File

_project_specs/session/current-state.md - Update every 15-20 minutes or after significant progress.

# Current Session State

*Last updated: 2025-01-15 14:32*

## Active Task
[One sentence: what are we working on right now]

Example: Implementing user authentication flow with JWT tokens

## Current Status
- **Phase**: [exploring | planning | implementing | testing | debugging | refactoring]
- **Progress**: [X of Y steps complete, or percentage]
- **Blocking Issues**: [None, or describe blockers]

## Context Summary
[2-3 sentences summarizing the current state of work]

Example: Created auth middleware and login endpoint. JWT signing works.
Currently implementing token refresh logic. Need to add refresh token
rotation for security.

## Files Being Modified
| File | Status | Notes |
|------|--------|-------|
| src/auth/middleware.ts | Done | JWT verification |
| src/auth/refresh.ts | In Progress | Token rotation |
| src/auth/types.ts | Done | Token interfaces |

## Next Steps
1. [ ] Complete refresh token rotation in refresh.ts
2. [ ] Add token blacklist for logout
3. [ ] Write integration tests for auth flow

## Key Context to Preserve
- Using RS256 algorithm (not HS256) per security requirements
- Refresh tokens stored in HttpOnly cookies
- Access tokens: 15 min, Refresh tokens: 7 days

## Resume Instructions
To continue this work:
1. Read src/auth/refresh.ts - currently at line 45
2. The rotateRefreshToken() function needs error handling
3. Check decisions.md for why we chose RS256 over HS256

Decision Log

_project_specs/session/decisions.md - Append-only log of architectural and implementation decisions.

# Decision Log

Track key decisions for future reference. Never delete entries.

---

## [2025-01-15] JWT Algorithm Choice

**Decision**: Use RS256 instead of HS256 for JWT signing

**Context**: Implementing authentication system

**Options Considered**:
1. HS256 (symmetric) - Simpler, single secret
2. RS256 (asymmetric) - Public/private key pair

**Choice**: RS256

**Reasoning**:
- Allows token verification without exposing signing key
- Better for microservices (services only need public key)
- Industry standard for production systems

**Trade-offs**:
- Slightly more complex key management
- Larger token size

**References**:
- src/auth/keys/ - Key storage
- docs/security.md - Security architecture

---

## [2025-01-14] Database Schema Approach

**Decision**: Use Drizzle ORM with PostgreSQL

**Context**: Setting up data layer

**Options Considered**:
1. Prisma - Popular, good DX
2. Drizzle - Type-safe, SQL-like
3. Raw SQL - Maximum control

**Choice**: Drizzle

**Reasoning**:
- Better TypeScript inference than Prisma
- More transparent SQL generation
- Lighter weight, faster cold starts

**References**:
- src/db/schema.ts - Schema definitions
- src/db/migrations/ - Migration files

Code Landmarks

_project_specs/session/code-landmarks.md - Important code locations for quick reference.

# Code Landmarks

Quick reference to important parts of the codebase.

## Entry Points
| Location | Purpose |
|----------|---------|
| src/index.ts | Main application entry |
| src/api/routes.ts | API route definitions |
| src/workers/index.ts | Background job entry |

## Core Business Logic
| Location | Purpose |
|----------|---------|
| src/core/auth/ | Authentication system |
| src/core/billing/ | Payment processing |
| src/core/workflows/ | Main workflow engine |

## Configuration
| Location | Purpose |
|----------|---------|
| src/config/index.ts | Environment config |
| src/config/features.ts | Feature flags |
| drizzle.config.ts | Database config |

## Key Patterns
| Pattern | Example Location | Notes |
|---------|------------------|-------|
| Service Layer | src/services/user.ts | Business logic encapsulation |
| Repository | src/repos/user.ts | Data access abstraction |
| Middleware | src/middleware/auth.ts | Request processing |

## Testing
| Location | Purpose |
|----------|---------|
| tests/unit/ | Unit tests |
| tests/integration/ | API tests |
| tests/e2e/ | End-to-end tests |
| tests/fixtures/ | Test data |

## Gotchas & Non-Obvious Behavior
| Location | Issue | Notes |
|----------|-------|-------|
| src/utils/date.ts | Timezone handling | Always use UTC internally |
| src/api/middleware.ts:45 | Auth bypass | Skip auth for health checks |
| src/db/pool.ts | Connection limit | Max 10 connections in dev |

CLAUDE.md Session Rules

Add this section to CLAUDE.md:

## Session Management

**IMPORTANT**: Follow session-management.md skill. Update session state at natural breakpoints.

### After Every Task Completion
Ask yourself:
1. Was a decision made? → Log to `decisions.md`
2. Did this take >10 tool calls? → Full checkpoint to `current-state.md`
3. Is a major feature complete? → Create archive entry
4. Otherwise → Quick update to `current-state.md`

### Checkpoint Triggers
**Quick Update** (current-state.md):
- After any todo completion
- After small changes

**Full Checkpoint** (current-state.md + decisions.md):
- After significant changes
- After ~20 tool calls
- After any decision
- When switching focus areas

**Archive** (archive/ + full checkpoint):
- End of session
- Major feature complete
- Context feels heavy

### Session Start Protocol
When beginning work:
1. Read `_project_specs/session/current-state.md`
2. Check `_project_specs/todos/active.md`
3. Review recent `decisions.md` entries if needed
4. Continue from "Next Steps"

### Session End Protocol
Before ending or when context limit approaches:
1. Create archive: `_project_specs/session/archive/YYYY-MM-DD.md`
2. Update current-state.md with handoff format
3. Ensure next steps are specific and actionable

Compression Strategies

When to Compress (Tier 3 Archive)

What to Keep vs Archive

Keep in active context:

• Current task and immediate next steps
• Active file list with status
• Blocking issues
• Key decisions affecting current work

Archive/summarize:

• Exploration paths that didn't work out
• Detailed debugging traces (keep conclusion only)
• Verbose error messages (keep root cause only)
• Research notes (keep recommendations only)

Compression Template

When compressing, use this format:

## Compressed Context - [Topic]

**Summary**: [1-2 sentences]

**Key Findings**:
- [Bullet points of important discoveries]

**Decisions Made**:
- [Reference to decisions.md entries]

**Relevant Code**:
- [File:line references]

**Archived Details**: [Link to archive file if created]

Session Archive

After significant work or at session end, create archive:

_project_specs/session/archive/YYYY-MM-DD[-topic].md

# Session Archive: [Date] - [Topic]

## Summary
[Paragraph summarizing what was accomplished]

## Tasks Completed
- [TODO-XXX] Description - Done
- [TODO-YYY] Description - Done

## Key Decisions
- [Reference decisions.md entries made this session]

## Code Changes
| File | Change Type | Description |
|------|-------------|-------------|
| src/auth/login.ts | Created | Login endpoint |
| src/auth/types.ts | Modified | Added RefreshToken type |

## Tests Added
- tests/auth/login.test.ts - Login flow tests
- tests/auth/refresh.test.ts - Token refresh tests

## Open Items Carried Forward
- [Anything not finished, now in active.md]

## Session Stats
- Duration: ~3 hours
- Tool calls: ~120
- Files modified: 8
- Tests added: 12

Integration with Todo System

Link Todos to Sessions

In active todos, reference session context:

## [TODO-042] Implement token refresh

**Status:** in-progress
**Session Context:** See current-state.md

### Progress Notes
- 2025-01-15: Started implementation, base structure done
- 2025-01-15: Added rotation logic, need error handling

Auto-Update on Todo Completion

When completing a todo:

1. Mark todo complete in active.md
2. Update current-state.md progress
3. Log any decisions made
4. Update code-landmarks.md if new patterns introduced

Quick Commands

Add to project scripts or aliases:

# Show current session state
alias session-status="cat _project_specs/session/current-state.md"

# Quick edit session state
alias session-edit="$EDITOR _project_specs/session/current-state.md"

# View recent decisions
alias decisions="tail -100 _project_specs/session/decisions.md"

# Create session archive
session-archive() {
  cp _project_specs/session/current-state.md \
     "_project_specs/session/archive/$(date +%Y-%m-%d).md"
  echo "Archived to _project_specs/session/archive/$(date +%Y-%m-%d).md"
}

Enforcement Mechanisms

1. CLAUDE.md as Entry Point

CLAUDE.md must reference session-management.md in the Skills section. Claude reads CLAUDE.md first, which directs it to follow session rules.

2. Session File Headers with Reminders

Include enforcement reminders in session file headers:

current-state.md header:

<!--
CHECKPOINT RULES (from session-management.md):
- Quick update: After any todo completion
- Full checkpoint: After ~20 tool calls or decisions
- Archive: End of session or major feature complete
-->

3. Self-Check Questions

After completing any task, Claude should ask:

□ Did I make a decision? → Log it
□ Did this take >10 tool calls? → Full checkpoint
□ Is a feature complete? → Archive
□ Am I ending/switching context? → Archive + handoff

4. Session Start Verification

When starting a session, Claude must:

1. Check if current-state.md exists and read it
2. Announce what it found: "Resuming from: [last state]"
3. Confirm next steps before proceeding

5. Periodic Self-Audit

Every ~20 tool calls, Claude should check:

• Is current-state.md up to date?
• Are there unlogged decisions?
• Is context getting heavy?

6. User Prompts

Users can enforce by asking:

• "Update session state" → Triggers checkpoint
• "What's the current state?" → Claude reads and reports
• "End session" → Triggers archive + handoff
• "Resume from last session" → Claude reads state files first

Anti-Patterns

• No state tracking - Flying blind, can't resume
• Overly verbose state - Keep it scannable, not a novel
• Stale state files - Update regularly or they become useless
• Missing decisions - Future you won't remember why
• No code landmarks - Wastes time re-discovering the codebase
• Never archiving - Session files become cluttered
• Ignoring compression signals - Context overload degrades performance
• Skipping checkpoint after decisions - Key context lost
• No handoff at session end - Next session starts blind

Quick Reference

Checkpoint Decision Tree

Task completed?
    │
    ├── Decision made? ──────────────────→ Log to decisions.md
    │
    ├── >10 tool calls OR significant? ──→ Full Checkpoint
    │
    ├── Major feature done? ─────────────→ Archive
    │
    └── Otherwise ───────────────────────→ Quick Update

Files at a Glance