checkpoint

Reconciles backlog, memory, and docs, then writes a hand-off doc and catch-up prompt at session boundaries.

Updated Jun 24, 2026
One-click install
npx skills add https://github.com/kashman001/ai-workspace-template --skill checkpoint-kashman001
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: checkpoint
Source: https://github.com/kashman001/ai-workspace-template/tree/main/skills/checkpoint
Command: npx skills add https://github.com/kashman001/ai-workspace-template --skill checkpoint-kashman001

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve? When an AI-assisted work session ends or the context window is about to be compacted, decisions, progress, and next steps are easily lost. This Skill wraps up a finished chunk of work so the next session resumes cleanly without the user re-explaining everything. ## Core Features & Use Cases - Record reconciliation: Marks finished items Done in the issue tracker/backlog, updates project memory and MEMORY.md pointers, syncs reference docs, and promotes flagged decision notes into ADRs. - Hand-off document generation: Drafts a hand-off doc under work/<project-name>/ that references artifacts by path, suggests skills for the next session, and redacts secrets. - State verification and catch-up prompt: Confirms clean git/branch state (including untracked work/ files) and emits a ready-to-paste catch-up prompt for the post-compaction session. - Use Case: After shipping a feature phase, say "checkpoint" before running /compact — the Skill updates the backlog, writes the hand-off doc, and gives you a 3-5 line prompt to paste into the fresh session. ## Quick Start Tell the agent "checkpoint" when finishing a chunk of work, optionally naming the next focus such as "checkpoint, next focus is Phase 3 Trends".

Frequently Asked Questions about checkpoint

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I hand off work between AI coding sessions without losing context?▼

Run the checkpoint skill at the end of a work chunk. It reconciles your backlog and project memory, writes a hand-off doc under work/<project-name>/, and emits a short catch-up prompt you paste into the next session after compacting context.

What should I do before compacting or clearing the context window?▼

Trigger a checkpoint before running /compact or your runtime's equivalent. The skill captures durable decisions as ADRs, updates memory pointers, and records branch state so nothing is lost when the context window resets.

When should I use checkpoint versus session-rollover?▼

Use session-rollover when a context-budget WARN/STOP signal fires, since measurement wins. Use checkpoint for a deliberate end of a work chunk when the budget is fine; if both apply, session-rollover takes precedence.

Does checkpoint work with GitHub Issues or only custom backlogs?▼

It works with whatever issue-tracker convention the repo uses — GitHub Issues, a BACKLOG.md, or .scratch/ — following docs/agents/issue-tracker.md if configured, otherwise the repository's own convention.

Why does the next session miss untracked work/ state files?▼

A new manifest or tracker left untracked makes the next session see a clean tree with no file. Checkpoint runs git status --short work/ and commits or explicitly notes any untracked state files to prevent this.