Checkpoint

Checkpoint Skill

You are saving session progress to a checkpoint file. This enables resumption after context compaction, session end, or context reset.

Purpose

Checkpoints provide:

• Work continuity across sessions
• Recovery from context loss
• Progress backup before risky operations
• Handoff preparation for context reset

When to Checkpoint

Automatic Triggers:

• Before major refactoring
• After completing significant work
• Before context-heavy operations
• Pre-compact hook (automatic)

Manual Triggers:

• User calls /checkpoint
• Before ending a session
• When switching tasks mid-stream

Checkpoint Process

/checkpoint [message]
     |
     +--[1] Gather session state
     |       - Current task
     |       - Files modified
     |       - Decisions made
     |       - Open questions
     |
     +--[2] Write checkpoint file
     |       - .claude/checkpoint.md
     |       - Timestamp
     |       - Full context dump
     |
     +--[3] Confirm save
             - Show summary
             - Offer to continue or exit

Checkpoint File Structure

# Checkpoint: [timestamp]

## Session Info
- Started: [session start time]
- Saved: [checkpoint timestamp]
- Duration: [elapsed time]

## Current Task
[Description of active task]

## Work Completed
### Done
- [item 1]
- [item 2]

### In Progress
- [item 3] - [status/notes]

### Blocked
- [item 4] - [blocker description]

## Files Modified
| File | Status | Changes |
|------|--------|---------|
| path/to/file.py | modified | [summary] |
| path/to/other.py | created | [summary] |

## Key Decisions
1. [Decision] - [rationale]
2. [Decision] - [rationale]

## Open Questions
- [question 1] - [context/impact]
- [question 2] - [context/impact]

## Next Steps
1. [immediate next action]
2. [following action]
3. [future consideration]

## Commands to Resume
```bash
# To resume this checkpoint:
/resume [checkpoint-id]

# Or run:
/start

Context Snapshot

[Recent conversation summary - key points only]

Git State

• Branch: [current branch]
• Uncommitted: [yes/no - count of files]
• Last commit: [hash] [message]

## Implementation Steps

### Step 1: Collect Context

1. Read conversation history (last N exchanges)
2. Identify active task from context
3. List all files read/modified this session
4. Capture key decisions and rationale
5. Note open questions and blockers

### Step 2: Generate Checkpoint

1. Create checkpoint directory if needed
2. Write checkpoint file with timestamp
3. Include all sections from template
4. Add git status if in repo

### Step 3: Confirm

CHECKPOINT SAVED

ID: checkpoint-[timestamp] File: .claude/checkpoint.md

Summary:

• Task: [active task]
• Files: [count] modified
• Duration: [session duration]

Options:

1. Continue working
2. End session (checkpoint preserved)
3. Create handoff artifact (for context reset)

## Checkpoint Management

### Checkpoint Rotation

Keep last N checkpoints (configurable, default 5):

.claude/ checkpoints/ checkpoint-2024-01-15-001.md checkpoint-2024-01-15-002.md checkpoint-2024-01-15-003.md (newest)

### Checkpoint Cleanup

- Auto-delete checkpoints older than 7 days
- Keep named checkpoints indefinitely
- Archive checkpoints when handoff created

## Integration with Context Reset

Before context reset, checkpoint automatically:

1. /checkpoint "pre-context-reset"
2. Create handoff artifact from checkpoint
3. Fresh session loads handoff
4. Continue without lost context

## Usage

/checkpoint # Save with auto-message /checkpoint "pre-refactor" # Save with description /checkpoint --named "v1" # Save named checkpoint /checkpoint --list # List all checkpoints

## Output

CHECKPOINT CREATED

ID: cp-2024-01-15-143052 File: .claude/checkpoints/cp-2024-01-15-143052.md

Task: Implementing user authentication Progress: 60% complete Files: 4 modified, 2 created

Resume with: /resume cp-2024-01-15-143052

## Error Handling

CHECKPOINT FAILED

Error: [error description] Recovery: [suggested fix]

Partial save available at: .claude/checkpoint-partial.md Manual intervention may be needed.

## Integration Points

- **With /start**: Loads checkpoints on session start
- **With /resume**: Loads specific checkpoint by ID
- **With pre-compact hook**: Called automatically before context compaction
- **With session-stop hook**: Saves final checkpoint on session end