breakpoint

/breakpoint — Session pickup prompt

A breakpoint captures everything a fresh session needs to resume without re-reading the whole transcript, in one structured block. The output is the deliverable: it goes into the conversation and is persisted to a dated file so it survives /compact or seeds the next session even if the conversation context is lost entirely.

Direction is forward and lateral: what's done, what's in flight, what's blocked, where to pick up.

This repo is course materials, not shipping software — so "work in flight" means an active grading pass, a docs/decisions/ memo mid-draft, or a course restructure, not a CI pipeline. The inputs below are retargeted accordingly.

When to break

Strong signals to checkpoint (the skill should fire on any of these):

• The user says "pickup prompt", "breakpoint", "hand off", "checkpoint", or is about to /compact / /clear.
• A grading pass is mid-flight — STAGE{N}_GRADES.md partially written, some students scored and some not.
• End of a phase — a course restructure or a multi-file git mv just landed, before starting the next.
• Before a risky operation — a git mv restructure of courses/, an archive move, a force-push, a worktree teardown.
• Context is getting long and a compaction is likely.

When in doubt, ask; don't force it.

Inputs (gather in this order; skip a line silently if the command errors or returns nothing)

1. Current branch + worktree state. git branch --show-current, git status --short, git worktree list. Note which branch each worktree holds. Count worktrees and flag concurrent-session hazards — more than a couple usually means another session shares the repo; a worktree nested inside .claude/ is the nested-creation gotcha.
2. Uncommitted / unpushed work — scope to THIS session's branch, not all local branches.
   • Dirty tree: git status --short.
   • Unpushed commits on the current branch: git rev-list --count @{u}..HEAD (or git log @{u}..HEAD --oneline); if there's no upstream, the branch itself is unpushed.
   • Do NOT use git log --branches --not --remotes — it sweeps every local branch (including other sessions' work) and produces a misleading pile of "unpushed commits" that isn't yours.
   • Unpushed work is the highest-loss-risk state — surface it first, but only the work that's actually yours.
   • Untracked stray files (git status --short ?? lines) — this repo routinely has untracked .claude/worktrees/ and draft memos; note which are intentional scratch vs. work that needs committing, so the next session doesn't blind-git add.
3. Open PRs + their state. If gh is available: gh pr list --state open --author "@me" --json number,title,headRefName,baseRefName,isDraft and, for each relevant PR, gh pr checks <n>. Capture stack relationships (base → head) explicitly.
4. Recently merged PRs (last ~24h or this session): gh pr list --state merged --limit 10 --json number,title,mergedAt — so the next session doesn't re-do landed work.
5. Task list state. Read the current task list (in-progress / pending / completed). If empty but work is clearly mid-flight, reconstruct from the transcript.
6. In-flight decision memos + plans. Glob docs/decisions/*.md (most recent first); flag any with status: proposed that this session is executing or that await ratification. Quote the memo's open question, don't paraphrase.
7. Active grading passes. If a grading task is live: which offering, which stage, which STAGE{N}_GRADES.md, how many students scored vs. remaining, whether the post-deadline sweep has run (feedback_regrade_policy — a stage locks once its sweep runs). Never copy score numbers into the pickup block (feedback_score_privacy — scores live only in the internal grades file and instructor email).
8. Standing constraints. Grading/house rules governing the current work (relevant feedback_* memories, a locked decision memo). Quote the constraint.