Re-Entry & End-of-Session Prompts

These two templates are halves of one system. The End-of-Session prompt writes docs/STATUS.md; the Re-Entry prompt reads it. Run the first one faithfully and the second one feels like magic. Skip the first and the second has nothing to work with — that's the whole deal.

The End-of-Session prompt — run it last, every time

End-of-Session prompt — the last message of every session
We're ending this session. Close it out properly:

1. Overwrite docs/STATUS.md with: date; what we accomplished today (3-6 bullets); exact current state (what works, what's half-done); the precise next step with enough detail that a fresh session could start it cold; any open questions/decisions pending.

2. Update checkboxes in docs/TODO.md. If we made a notable technical choice today, append one line to docs/DECISIONS.md (choice + why).

3. git status — if anything is uncommitted, either commit it with a clear message or stash it and NOTE THAT in STATUS.md.

4. Show me STATUS.md so I can confirm it's accurate.

Two minutes, and it pays for itself tenfold. The details that matter:

  • "Overwrite" — STATUS.md is a snapshot, not a diary. The old status is obsolete the moment there's a new one; history lives in Git, not in the file.
  • "…enough detail that a fresh session could start it cold" — the quality bar for the next-step line. "Continue search feature" fails it; "wire the search input in Header.astro to the /api/search endpoint; the endpoint works, the input is still static" passes.
  • The commit-or-stash step kills the #1 returning-developer confusion: mystery uncommitted changes. Future-you either finds clean state, or finds a note explaining exactly what was left dangling and why.

The Grand Re-Entry prompt — after days or weeks away

Grand Re-Entry prompt — when you can't remember where things stand
I'm returning to this project after time away. Rebuild context EFFICIENTLY — do not read the whole codebase.

1. Read CLAUDE.md, docs/STATUS.md, and docs/TODO.md.

2. Run: git log --oneline -15  and  git status — note any uncommitted work or surprise branches.

3. Run the build ([npm run build]) to confirm the project is healthy; if it fails, report the error but don't fix yet.

4. Then brief me in under 20 lines:
   • What this project is (1-2 lines)
   • Where we left off + what the last 5 commits did
   • Anything unfinished/uncommitted right now
   • The top 3 next actions from TODO.md
   • Any risk or open question I should decide on

5. STOP after the briefing. Wait for me to pick the next task.

Why it works: STATUS + TODO + the git log are the project's state — the source code is just the implementation of that state. Reading three small files and fifteen commit messages costs about 2% of reading the source and gives you (and Claude) 98% of the orientation.

  • The build check answers "is anything broken?" before you plan anything — but "report, don't fix yet" keeps the session from wandering off.
  • The hard STOP matters. Re-entry sessions that immediately start coding tend to code the wrong thing. First the briefing, then you pick the task.
  • Older project without STATUS.md? Say so, and add a step 6: "Since docs/STATUS.md doesn't exist, create the docs/ memory system now based on what you learned, then give the briefing." The system bootstraps itself onto any existing repo.

The moment it clicks: the first time Claude briefs you on your own project — what it is, where you left off, what's next — in twenty seconds, you'll understand why this handbook keeps insisting that files are memory. Run the End-of-Session prompt today; tomorrow-you gets the demo.

Up next: two prompts that make you better, not just faster — Teacher mode for understanding what got built, and the review prompt that finds what a senior dev would flag.

FAQ

Frequently Asked Questions

What does the End-of-Session prompt do?
As the last message of a session it makes Claude overwrite docs/STATUS.md (accomplishments, exact current state, precise next step, open questions), update TODO checkboxes, log notable decisions, and commit or stash anything uncommitted — a two-minute handoff to future-you.
What is the Grand Re-Entry prompt?
The prompt for returning after time away: Claude reads CLAUDE.md + STATUS + TODO, checks git log and git status, runs the build, then briefs you in under 20 lines and stops so you pick the next task. Orientation without re-reading the codebase.
Why does the Re-Entry prompt end with STOP?
Re-entry sessions that immediately start coding tend to code the wrong thing. The briefing first, then a human decision — that order is the point.
What if my project has no STATUS.md yet?
Say so and add a step: "Since docs/STATUS.md doesn't exist, create the docs/ memory system now based on what you learned, then give the briefing." The system bootstraps onto any existing repository.