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".