Wrap Session

Session Wrap

Capture the current session's context and produce two things:

1. Persistent documentation — updated or created in the project's own style
2. A continuation prompt — a self-contained message that lets the next chat pick up exactly where this one ends

Philosophy

You are intelligent. Don't follow a rigid template — think about what matters for this specific session and project. The goal is: if someone opens a fresh chat tomorrow with zero context, what do they need to seamlessly continue?

Step 1: Discover the Project's Documentation Conventions

Before writing anything, understand how this project already documents things:

• Look for existing patterns: session summaries, ADRs, changelogs, README, CLAUDE.md, ai/memory/, docs/, decision logs, plan files
• Check git log for recent documentation commits
• Note the naming conventions, file locations, and formats already in use

Adapt to what exists. If the project uses ADRs, update ADRs. If it uses session summaries, create the next one. If nothing exists, create something minimal and well-placed.

Step 2: Capture What Matters

Reflect on the full conversation and extract:

• What was accomplished — decisions made, files created/modified, problems solved
• What's still open — unresolved questions, next steps, blockers
• Critical context — things the next session must know that aren't obvious from the code alone (rationale, rejected approaches, user preferences, constraints discovered)
• The exact pickup point — what specific task or question should the next session start with

Be ruthless about signal vs noise. Only capture what a smart engineer with access to the codebase couldn't figure out on their own.

Step 3: Write Project Documentation

Update or create documentation using the project's conventions:

• Update existing files that track progress (session summaries, plans, decision logs)
• Create new files only if the project's pattern calls for it (e.g., a new session summary in a series)
• Keep it scannable — bullets, tables, clear headers. A reader should get 80% of the value in 30 seconds.

If no conventions exist, create a single SESSION-HANDOFF.md at the project root.

Step 4: Generate Continuation Prompt

Create a prompt the user can paste into a new chat. This is the most important output.

The prompt should:

• Set the role and mission — what kind of work is being done
• Point to prerequisite files — what to read first (be specific with paths)
• State what's already decided — so the next session doesn't re-debate settled questions
• Define the pickup point — the exact next step, framed as an actionable instruction
• Be self-contained — the prompt alone (plus the files it references) should be enough

Write it in the voice of the user giving instructions to a new collaborator. Make it feel natural, not robotic.

Output

Present to the user:

1. Session summary — 3-5 sentences of what happened
2. Files written/updated — list with paths
3. The continuation prompt — ready to copy-paste, in a code block