Context Persistence Skill

Purpose

Ensure Claude Code can resume work seamlessly after context resets, session interruptions, or long breaks by maintaining structured documentation of current work, decisions, and progress.

When to Use This Skill

Automatically activates when you mention:

• Waypoint plans, waypoint planning
• Resuming work, continuing work
• Session survival, context reset
• Task handoff, progress tracking
• Long-running features or projects
• Need to document current state

The Problem: Context Resets

What happens during a context reset:

• ❌ All conversation history lost
• ❌ Current task context forgotten
• ❌ Decisions and rationale gone
• ❌ Progress not tracked
• ❌ Have to re-explain everything

With context persistence:

• ✅ Current task documented
• ✅ Decisions and rationale preserved
• ✅ Progress clearly tracked
• ✅ Quick resume in < 1 minute
• ✅ Seamless handoff to future sessions

---

Three-File Structure

The core pattern uses three complementary files in plans/active/{task-name}/:

1. {task-name}-plan.md - The Strategic Plan

Purpose: High-level strategy and approach

Contains:

• Feature/task overview
• Requirements and acceptance criteria
• Architecture approach
• Implementation phases
• Dependencies and constraints
• Risks and mitigations

Update frequency: Rarely (only when approach changes)

Example:

# Authentication Implementation Plan

## Overview
Add JWT-based authentication to replace session cookies for mobile app support.

## Requirements
- JWT tokens with refresh mechanism
- Supabase Auth integration
- Protected API routes
- Mobile-friendly (stateless)

## Architecture
- Auth middleware in Edge Functions
- Token storage in httpOnly cookies (web) + AsyncStorage (mobile)
- Row-Level Security policies for data access

## Implementation Phases
1. Supabase Auth setup
2. Edge Function auth middleware
3. Frontend auth hooks
4. RLS policies
5. Migration from existing auth

## Dependencies
- Supabase setup complete
- Database schema finalized

2. {task-name}-context.md - Current State & Progress

Purpose: Living document of current state, decisions, and progress

Contains:

• SESSION PROGRESS (updated frequently)
• Key decisions made
• Important discoveries
• Current blockers
• Files modified
• Quick resume instructions

Update frequency: After each significant change or decision

Example:

# Authentication Implementation Context

## SESSION PROGRESS (2025-01-15 14:30)

### ✅ COMPLETED
- [x] Supabase Auth configured
- [x] Created auth middleware for Edge Functions
- [x] Implemented login/signup pages
- [x] Added auth context provider

### 🟡 IN PROGRESS
- [ ] Implementing token refresh logic (CURRENT)
  - Working on: lib/supabase/auth.ts
  - Next: Handle token expiration gracefully

### ⏳ PENDING
- [ ] Add RLS policies
- [ ] Migrate existing users
- [ ] Add mobile auth flow
- [ ] Write auth tests

### 🎯 NEXT ACTION
Continue implementing refreshToken() function in lib/supabase/auth.ts
- Handle expired tokens
- Refresh transparently
- Redirect to login if refresh fails

## KEY DECISIONS

### Decision: JWT vs. Session Cookies (2025-01-12)
**Chose**: JWT tokens
**Rationale**: Need stateless auth for mobile apps
**Impact**: Requires token refresh mechanism

### Decision: Supabase Auth vs. Custom (2025-01-13)
**Chose**: Supabase Auth
**Rationale**: Built-in RLS integration, handles token refresh
**Impact**: Less custom code, tighter Supabase integration

## IMPORTANT DISCOVERIES

### Token Refresh Timing
Discovered tokens expire after 1 hour by default. Need to:
- Refresh proactively at 50 minutes
- Handle edge case of offline user
- Store refresh token securely

### RLS Row vs. Column Level
Supabase RLS is row-level only, not column-level.
For sensitive columns, need separate tables.

## CURRENT BLOCKERS

None currently. Auth flow is straightforward with Supabase.

## FILES MODIFIED

### Created
- lib/supabase/auth.ts (auth utilities)
- app/(auth)/login/page.tsx
- app/(auth)/signup/page.tsx
- components/auth/auth-provider.tsx

### Modified
- lib/supabase/client.ts (added auth hooks)
- middleware.ts (added auth middleware)

## QUICK RESUME

To continue this work:
1. Read this file (context.md) for current state
2. Check tasks.md for checklist
3. Refer to plan.md for overall strategy
4. Current file: lib/supabase/auth.ts
5. Next: Implement refreshToken() function
6. After that: Test token refresh flow

3. {task-name}-tasks.md - Actionable Checklist

Purpose: Granular, actionable tasks with acceptance criteria

Contains:

• Detailed task breakdown
• Acceptance criteria for each task
• Dependencies between tasks
• Task status (pending/in-progress/complete)

Update frequency: Daily or after completing tasks

Example:

# Authentication Implementation Tasks

## Phase 1: Supabase Setup ✅

- [x] Create Supabase project (Acceptance: Project created, credentials stored)
- [x] Enable Email auth provider (Acceptance: Can sign up via email)
- [x] Configure redirect URLs (Acceptance: Auth callbacks work locally + prod)
- [x] Add auth schema to database (Acceptance: Users table exists)

## Phase 2: Backend Auth 🟡

- [x] Create auth utilities (Acceptance: getUser(), signIn(), signUp() functions work)
- [ ] Implement token refresh **(IN PROGRESS)**
  - Acceptance: Tokens refresh automatically before expiry
  - Dependencies: Auth utilities complete
  - Notes: Need to handle offline case
- [ ] Add auth middleware to Edge Functions
  - Acceptance: Protected routes return 401 if not authenticated
  - Dependencies: Token refresh working
- [ ] Create auth helper for server components
  - Acceptance: Can check auth in Server Components

## Phase 3: Frontend Auth ⏳

- [x] Create auth context provider (Acceptance: Auth state available app-wide)
- [x] Build login page (Acceptance: Can log in with email/password)
- [x] Build signup page (Acceptance: Can create account)
- [ ] Add protected route wrapper
  - Acceptance: Redirects to login if not authenticated
  - Dependencies: Auth context complete
- [ ] Add loading states
  - Acceptance: Shows loading spinner during auth checks

## Phase 4: Security 🔒

- [ ] Add RLS policies
  - Acceptance: Users can only access their own data
  - Files: supabase/migrations/xxx_rls_policies.sql
- [ ] Test auth edge cases
  - Expired tokens
  - Invalid tokens
  - Network failures
  - Concurrent sessions

## Phase 5: Migration 📦

- [ ] Create migration script for existing users
- [ ] Test migration locally
- [ ] Schedule maintenance window
- [ ] Execute migration in production
- [ ] Verify all users migrated successfully

---

SESSION PROGRESS Pattern

The SESSION PROGRESS section is the most important part of context.md:

Structure

## SESSION PROGRESS (2025-01-15 14:30)

### ✅ COMPLETED
[What's done - be specific]

### 🟡 IN PROGRESS
[What you're working on RIGHT NOW]

### ⏳ PENDING
[What's coming next]

### 🚫 BLOCKED
[What's preventing progress - if any]

### 🎯 NEXT ACTION
[Specific next step with file + function]

Best Practices

DO ✅:

• Update after each significant milestone
• Be specific about current file/function
• Include "NEXT ACTION" for easy resume
• Mark completed items immediately
• Note blockers as they arise

DON'T ❌:

• Leave stale progress (update regularly)
• Be vague ("working on auth" → "implementing refreshToken() in auth.ts")
• Forget to mark completed items
• Skip the NEXT ACTION (critical for resume)

Update Frequency

Event	Update SESSION PROGRESS?
Completed a full task	✅ Yes
Significant decision made	✅ Yes
Discovered blocker	✅ Yes
Changed approach	✅ Yes
Switching to different task	✅ Yes
Minor code change	❌ No
Formatting/cleanup	❌ No
Reading code	❌ No

---

Quick Resume Instructions

Always include this section in context.md:

## QUICK RESUME

To continue this work:
1. **Read**: This file (context.md) for current state
2. **Check**: tasks.md for detailed checklist
3. **Reference**: plan.md for overall strategy
4. **Current file**: [exact file path]
5. **Current function**: [exact function/component name]
6. **Next step**: [specific action to take]
7. **After that**: [following step]
8. **Expected time**: [estimate for next step]

### If Context is Stale (> 3 days old)
1. Verify current code state matches context
2. Check for changes by others (git log)
3. Update context.md before proceeding

---

When to Create Waypoint Plans

Always Create For

✅ Features taking > 2 hours ✅ Multi-session work ✅ Complex implementations ✅ Work likely to be interrupted ✅ Team handoffs ✅ Refactorings affecting multiple files

Optional For

⚠️ Simple bug fixes (< 30 min) ⚠️ Documentation updates ⚠️ Minor UI tweaks ⚠️ Configuration changes

Never Create For

❌ Trivial changes ❌ Automated tasks ❌ One-liner fixes

Rule of Thumb: If you might forget context after lunch, create a waypoint plan.

---

Directory Structure

plans/
├── active/                      # Current work
│   ├── auth-implementation/
│   │   ├── auth-implementation-plan.md
│   │   ├── auth-implementation-context.md
│   │   └── auth-implementation-tasks.md
│   ├── payments-integration/
│   │   ├── payments-integration-plan.md
│   │   ├── payments-integration-context.md
│   │   └── payments-integration-tasks.md
│   └── README.md               # Active work index
├── archived/                   # Completed work
│   └── [moved completed tasks]
└── templates/                  # Templates for new tasks
    ├── template-plan.md
    ├── template-context.md
    └── template-tasks.md

---

File Naming Convention

Pattern: {task-slug}-{type}.md

Examples:

• auth-implementation-plan.md
• auth-implementation-context.md
• auth-implementation-tasks.md

task-slug:

• Lowercase
• Hyphen-separated
• Descriptive (not generic)
• Max 3-4 words

Good slugs:

• auth-implementation
• stripe-payments
• user-dashboard

Bad slugs:

• feature (too generic)
• task-123 (meaningless)
• implement_new_authentication_system_with_jwt (too long)

---

Commands for Claude Code Waypoint Plugin

Provide these commands:

# Create new waypoint plan
/create-plan [task-name]          # Creates 3-file structure

# Update existing waypoint
/update-context                   # Updates SESSION PROGRESS

# Resume work
/resume                           # Shows latest context + next action
/resume [task-name]               # Resume specific task

# Archive completed work
/archive [task-name]              # Moves to archived/

---

Integration with Commands

/create-plan Command

Creates the three-file structure automatically:

/create-plan auth-implementation

Creates:
- plans/active/auth-implementation/auth-implementation-plan.md
- plans/active/auth-implementation/auth-implementation-context.md
- plans/active/auth-implementation/auth-implementation-tasks.md

See the /create-plan command documentation for details.

/update-context Command

Updates SESSION PROGRESS section with prompts:

/update-context

Prompts:
- What did you complete?
- What are you currently working on?
- What's the specific file/function?
- What's the next action?
- Any blockers?

/resume Command

Displays context for quick resume:

/resume

Output:
📂 Resuming: auth-implementation
📋 CONTEXT SUMMARY:
- Last updated: 2 hours ago
- In progress: Implementing token refresh
✅ COMPLETED (3/8): ...
🟡 IN PROGRESS (1/8): ...
➡️ NEXT ACTION: Implement refreshToken() in lib/supabase/auth.ts

---

Best Practices

DO ✅

1. Update context after significant changes (not after every line)
2. Be specific in NEXT ACTION (file + function + what to do)
3. Mark tasks complete immediately (don't batch them)
4. Document decisions with rationale (the "why" not just "what")
5. Include code snippets in context (for complex logic)
6. Add timestamps to SESSION PROGRESS (know when it was updated)
7. Archive completed tasks (keep active/ directory clean)

DON'T ❌

1. Don't let context get stale (> 3 days without update = stale)
2. Don't be vague ("working on auth" tells you nothing)
3. Don't skip NEXT ACTION (critical for resuming)
4. Don't forget to update after decisions (decisions are context!)
5. Don't duplicate info (plan vs. context vs. tasks have different purposes)
6. Don't commit sensitive info (credentials, API keys)

---

Handling Context Staleness

Detecting Staleness

Context is stale if:

• Last updated > 3 days ago
• Code changed significantly since update
• Blocker was noted but not resolved
• IN PROGRESS task completed but not marked

Refreshing Stale Context

## Context Refresh Checklist

Before resuming stale context:
- [ ] Read current code in "current file"
- [ ] Check git log for changes since last update
- [ ] Verify IN PROGRESS task is actually in progress
- [ ] Update completed tasks
- [ ] Remove resolved blockers
- [ ] Update NEXT ACTION if changed
- [ ] Add note: "Context refreshed on [date]"

---

Example: Complete Context Lifecycle

Day 1: Create Waypoint Plan

User: "Let's implement JWT authentication"
Claude: "I'll create a waypoint plan for this task"
/create-plan auth-implementation

Creates 3 files with:
- Plan: Overall strategy
- Context: Empty SESSION PROGRESS
- Tasks: Broken down checklist

Day 1: Work & Update

After 2 hours of work:

## SESSION PROGRESS (2025-01-15 14:30)

### ✅ COMPLETED
- [x] Supabase Auth configured
- [x] Created auth utilities

### 🟡 IN PROGRESS
- [ ] Implementing login page

### 🎯 NEXT ACTION
Complete LoginForm component in app/(auth)/login/page.tsx

Day 2: Resume

User: "Continue with authentication"
Claude: /resume
→ Shows SESSION PROGRESS
→ "You were implementing LoginForm component"
→ Continues seamlessly

Day 3: Context Reset

Context reset happens (100K tokens)

User: "Continue with authentication"
Claude: /resume
→ Reads context.md
→ "I see you're implementing JWT auth"
→ "Last worked on: LoginForm component"
→ "Next action: Add form validation"
→ Continues without missing a beat

Day 5: Complete & Archive

User: "Authentication is done"
Claude: Updates all tasks to completed
/archive auth-implementation

Moves files to:
plans/archived/auth-implementation/

---

Summary

Claude Code Waypoint Plugin enables:

1. ✅ Seamless resume after context resets
2. ✅ Quick handoff between sessions
3. ✅ Clear progress tracking
4. ✅ Decision documentation
5. ✅ Team collaboration

Three-file structure:

• plan.md: Strategy (rarely changes)
• context.md: Current state (updated frequently)
• tasks.md: Actionable checklist (updated daily)

Key section: SESSION PROGRESS in context.md

Commands: /create-plan, /update-context, /resume

Rule: If work takes > 2 hours or spans multiple sessions, create a waypoint plan!

Use this skill to make Claude Code resilient to context resets and interruptions.