Session Wrap-Up

Persist all session-level learnings and state to disk BEFORE running /compact or ending a session. Ensures nothing is discarded with the conversation.

When to use

• At end-of-day / session end (user signals "we're done for today")
• Before running /compact (especially mid-sprint)
• After a long merge wave or planning session
• When approaching a token budget threshold (≥40% weekly)

Distinct from sprint-wrap-up which is for closing a sprint with retrospective + tagging. This skill is for routine session ends while a sprint is still active.

Step 1: Verify on main in /workspace

pwd && git branch --show-current

Must be /workspace on main. Abort if not.

Step 2: Append to plan/diary.md

Add a new ## YYYY-MM-DD HH:MM — <brief title> section at the bottom with:

• Pass rate — start and end numbers if changed
• Merges — PRs that landed, with net deltas
• Closes — PRs rejected, with reasons
• New issues filed — numbers + one-line purpose
• Incidents — OOM, stuck processes, false-positive regressions, CI glitches
• Context/budget — tokens burned, triggers, mitigations applied
• Key learnings — non-obvious findings worth saving (1-sentence each)

Keep it to ~30-60 lines. Bullets, not prose.

Step 3: Update plan/issues/sprints/N/sprint.md

Fill the ## Results section (mark as "interim" if sprint still active):

## Results (interim — YYYY-MM-DD, sprint still active)

**Baseline progress:** <start> → **<end>** pass / <total> total = **<pct>%** (<+delta>)
Sprint goal (<goal>) <met|not yet met>. <gap> tests <remaining>.

### Merged
- **#NNN <title>** (<PR>, <+delta> pass)
...

### Closed without merging
- **#NNN <reason>**
...

And if the sprint has a ## Retrospective section, append an interim retro with "What went well / What went badly / Process improvements / Key numbers / Sprint-close criteria remaining".

Step 4: Append the retrospective section in plan/issues/sprints/N/sprint.md

If a retrospective file doesn't exist yet, create one with frontmatter:

---
sprint: Sprint-N
status: interim | final
session_end: YYYY-MM-DD
---

# Sprint N Retrospective — INTERIM (sprint still active)

Then fill with the same what-went-well / badly / process-improvements sections. Mark "interim" clearly if sprint isn't closed yet.

Step 5: Update plan/agent-context/tech-lead.md

---
agent: tech-lead
session_end: YYYY-MM-DD
next_session_entry_point: read this file, then plan/issues/sprints/N/sprint.md
---

# Tech Lead Context Summary — YYYY-MM-DD

## Baseline state
## Sprint N status
  ### Merged today
  ### Closed
  ### PRs still in flight
  ### Unassigned ready work (prioritized)
## Team state
## Local state needing push
## Unfinished work / loose ends
## Entry points for next session

This file is what the NEXT session reads as its first tool call instead of claude --resume. Be thorough — ~100-200 lines of actionable bullets.

Step 6: Stage and commit

git add plan/diary.md plan/issues/sprints/N/sprint.md plan/agent-context/tech-lead.md
git diff --cached --stat
git commit -m "docs(session): end-of-session checkpoint — YYYY-MM-DD

✓

Persist session learnings to disk before /compact.
- plan/diary.md: <summary>
- plan/issues/sprints/N/sprint.md: <summary + retrospective updates>
- plan/agent-context/tech-lead.md: handoff for next session

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>"

Step 7: Push

git pull --rebase origin main 2>&1 | tail -3
git push origin main 2>&1 | tail -3

If the rebase gets stuck mid-pick with "editing commit" state, run git rebase --continue — it's a transient git state-machine glitch from empty-after-rebase detection.

Step 8: Tell the user

Short summary:

Pre-compact snapshot committed (<commit-hash>). Pushed.
Next session: read plan/agent-context/tech-lead.md, do NOT --resume this session.
Safe to /compact now.

Notes

• Never skip step 2 and 3. Diary + sprint doc are the persistent project log. Compacting without updating them loses the session's learnings permanently.
• tech-lead.md is NOT optional — it's the handoff channel that replaces session resume. Write it every time you end a long session.
• Don't wait for sprint close to fill retrospective sections. Interim retros are fine; the sprint doc carries multiple interim entries over time.
• Interim retro files are allowed — mark status: interim in the frontmatter. When the sprint closes, update to status: final and amend.