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Never lose context again. Strategic waypoints for persistent memory and intentional context management in Claude Code projects.

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Claude Code Waypoint

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Never lose context again. Strategic waypoints for persistent memory and intentional context management in Claude Code projects.


The Problem

Working with AI on complex projects means:

  • Context resets force you to start from scratch
  • Lost decisions - no record of why choices were made
  • Forgotten progress - can't remember what's done
  • Broken continuity - every session feels like day one
  • Manual repetition - explaining the same things over and over

The Solution

Claude Code Waypoint creates strategic checkpoints throughout your project journey:

  • Resume in < 60 seconds after any context reset
  • Persistent memory across sessions, days, weeks
  • Auto-activating skills provide the right context automatically
  • Decision logging captures the "why" behind choices
  • Works beyond code - planning, research, any long-running work

Waypoints are navigation markers that help you track progress, return to known points, and resume quickly from exactly where you left off.


🚀 Quick Start

Installation

Copy Claude Code Waypoint to your project:

# Clone this repository
git clone https://github.com/DojoCodingLabs/claude-code-waypoint

# Copy to your project
cp -r claude-code-waypoint/.claude /path/to/your/project/
cp -r claude-code-waypoint/plans /path/to/your/project/

# Set up hooks
cd /path/to/your/project/.claude/hooks
npm install && chmod +x *.sh

Your First Waypoint

# Create a waypoint for a feature
/create-plan auth-implementation

# Work on your feature...
# Waypoint tracks context automatically

# Before taking a break
/update-context

# Resume later (even after context reset)
/resume auth-implementation
# → Back to work in < 60 seconds

→ Detailed Installation Guide


📖 How to Use: The Waypoint Workflow

Step 1: Plan First (Think & Document)

Start by having Claude help you think through requirements:

/plan Build authentication system with OAuth and JWT

Claude will help you:

  • Clarify requirements and edge cases
  • Identify technical decisions
  • Consider architecture options
  • Document initial approach

Key Point: This is exploration mode. Ask questions, refine thinking, iterate.

Step 2: Create Official Waypoint (Formalize)

Once requirements are clear, formalize into waypoint structure:

/create-plan auth-system

This creates the 3-file waypoint:

plans/active/auth-system/
├── auth-system-plan.md      # Strategy & architecture
├── auth-system-context.md   # Current state & decisions
└── auth-system-tasks.md     # Actionable checklist

Claude will populate these based on your planning discussion.

Step 3: Review & Approve (Your Responsibility)

This is critical: You are the builder, you own the plan.

# Review the waypoint files
cat plans/active/auth-system/auth-system-plan.md

# Check if approach makes sense
# Verify architecture decisions align with your goals
# Ensure nothing critical is missing

Ask yourself:

  • Does this approach make sense for my project?
  • Are the trade-offs acceptable?
  • What could go wrong?

Approve explicitly:

"I've reviewed the auth-system plan and approve it. Let's proceed."

Step 4: Execute (Stay Context-Aware)

Now implement with Claude, maintaining context throughout:

# Claude implements based on approved plan
# Waypoint tracks progress automatically

# Before long breaks or context reset risk
/update-context

# After context reset
/resume auth-system
# → Back in < 60 seconds with full context

While executing:

  • Update waypoint when you discover new information
  • Log decisions and why they were made
  • Track what's completed vs pending
  • Document blockers as they appear

🎯 Core Features

1. Persistent Memory System (PRIMARY)

The 3-file waypoint structure captures everything:

plans/active/auth-implementation/
├── auth-implementation-plan.md      # Strategy (rarely changes)
├── auth-implementation-context.md   # Current state (updated frequently)
└── auth-implementation-tasks.md     # Actionable checklist (daily updates)

What gets tracked:

  • Decisions - Why you chose specific approaches
  • Progress - What's done, in progress, and pending
  • Blockers - What's preventing progress
  • Next actions - Specific file + function to work on
  • Key discoveries - Important findings during work

SESSION PROGRESS tracking enables the < 60 second resume:

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

### ✅ COMPLETED
- [x] Task 1 done
- [x] Task 2 done

### 🟡 IN PROGRESS
- [ ] Task 3 (CURRENT)

### 🎯 NEXT ACTION
Edit src/auth/login.ts - implement validateCredentials()

→ Deep dive: Waypoint Pattern

2. Auto-Activation System (CRITICAL)

Skills auto-activate based on context - right knowledge at the right time:

User types: "Create a new plan for..."
    ↓
Hook analyzes: prompt keywords + active files
    ↓
Auto-suggests: context-persistence skill
    ↓
Claude gets: Perfect context automatically

Key skills that auto-activate:

  • memory-management - When you need to remember preferences
  • context-persistence - When working with waypoint files
  • plan-approval - When making significant changes

→ Learn more: Auto-Activation System

3. Commands for Waypoint Management

  • /create-plan [task] - Create new waypoint (3-file structure)
  • /update-context - Update waypoint before context reset
  • /resume [task] - Resume from existing waypoint

4. Specialized Agents

Copy-and-use agents for common workflows:

  • scaffold-customizer - Adapt skills to your tech stack
  • documentation-architect - Generate comprehensive docs
  • code-architecture-reviewer - Review code for consistency
  • refactor-planner - Plan refactoring strategies
  • plan-reviewer - Review development plans
  • web-research-specialist - Research technical issues

→ View all agents


📚 What's Included

Core Skills (Memory & Context)

Skill Purpose
memory-management Intentional memory tracking and preference learning
context-persistence Waypoint pattern implementation
plan-approval User control workflows for complex changes

These work with any tech stack - they're methodology, not code.

Example Scaffolds (Opinionated)

Skill Tech Stack
frontend-dev-guidelines Next.js 14+ + React 19 + shadcn/ui
backend-dev-guidelines Supabase + Edge Functions

Not using our stack? Use the scaffold-customizer agent to adapt skills for your tech.

→ Customization guide

Skill Developer (Meta)

The skill-developer skill teaches you how to create custom skills with memory patterns.

→ Learn skill development


💡 Use Cases

🖥️ Software Development

Feature: Authentication refactor
Waypoint tracks:
- Current architecture decisions
- Migration progress (which files done)
- Blockers and workarounds discovered
- Testing approach and edge cases
- Performance benchmarks

Resume time: 45 seconds

📊 Business Planning

Project: Q1 strategy redesign
Waypoint tracks:
- Market research findings
- Stakeholder feedback
- Strategic options considered
- Resource allocation decisions
- Implementation timeline

Resume time: 30 seconds

🔬 Research Projects

Research: ML model optimization
Waypoint tracks:
- Experiment results
- Hyperparameter tuning notes
- Performance comparisons
- Dead ends and why they failed
- Next experiment hypotheses

Resume time: 60 seconds

The waypoint pattern works for any long-running work that requires persistent context.


🌟 Credits & Origin

This project packages the incredible work shared by diet103 in their repository claude-code-infrastructure-showcase.

Original Inspiration

From the Reddit post: "Claude Code is a Beast - Tips from 6 Months of Hardcore Use"

What We Did

Building on this foundation, we added our own twist and improvements:

  • Introduced the "Waypoint" metaphor - Renamed "dev docs" to "waypoints"
  • Transformed into distributable package - Proper repository structure
  • Enhanced documentation - Created comprehensive guides
  • Improved organization - Restructured as plans/ directory
  • Positioned correctly - Memory/context management as PRIMARY
  • Made it accessible - Simple copy-paste installation

Core credit goes to diet103 for the innovative infrastructure patterns and 6 months of real-world validation.


📖 Documentation

Getting Started

Advanced Usage

Technical Reference


🤝 Contributing

We welcome contributions! See CONTRIBUTING.md for guidelines.

Contributions welcome:

  • Bug fixes and improvements
  • New skills for different tech stacks
  • Documentation enhancements
  • Example waypoint templates

📄 License

MIT License - See LICENSE for details.


💬 Support


Built by Dojo Coding, for Builders.
Production-tested tools for serious Claude Code users.

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Never lose context again. Strategic waypoints for persistent memory and intentional context management in Claude Code projects.

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