Agent skill

wrap-session

End-of-session documentation workflow that updates README, CHANGELOG, agent context files, and creates session logs. Use when wrapping up a working session, when asked to document session progress, when preparing handoff documentation, or when the user says "wrap up", "end session", "document progress", or "save session".

View SKILL.md on GitHub Repository
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Install this agent skill to your Project

npx add-skill https://github.com/product-on-purpose/pm-skills/tree/main/.claude/skills/wrap-session

SKILL.md

Session Wrap-Up Workflow

Execute this workflow when ending a working session to maintain project continuity.

Execution Steps

1. Identify Project Root

Locate the project root containing README.md and CHANGELOG.md. If uncertain, ask the user.

2. Update README.md

Update the project description and status to reflect current state. Keep changes minimal — only update what has meaningfully changed.

3. Update CHANGELOG.md

Append changes to the [Unreleased] section using Keep a Changelog format. See references/changelog-format.md for format details.

Change categories:

  • Added — New features/files
  • Changed — Modified functionality
  • Fixed — Bug fixes
  • Deprecated — Soon-to-be removed
  • Removed — Deleted features
  • Security — Vulnerability fixes

If CHANGELOG.md doesn't exist, create it using assets/CHANGELOG.template.md.

4. Update Agent Context Files

Create/update files in AGENTS/<model>/ (e.g., AGENTS/claude/):

File Purpose When to Update
CONTEXT.md Current project state Always
TODO.md Task tracking When tasks change
DECISIONS.md Technical decisions When decisions are made

If AGENTS folder doesn't exist: Create the full structure:

AGENTS/
└── claude/
    ├── CONTEXT.md
    ├── TODO.md
    ├── DECISIONS.md
    ├── SESSION-LOG/
    └── PLANNING/

See references/context-files.md for file formats.

4b. Save Planning Artifacts (When Applicable)

If the session involved planning, review, or analysis work that produced artifacts requiring review, save them to AGENTS/<model>/PLANNING/:

When to create PLANNING documents:

  • Architecture proposals or design documents
  • Code review summaries and recommendations
  • Investigation reports and research findings
  • Implementation plans and roadmaps

File naming:

  • Use descriptive, kebab-case names: auth-system-design.md, api-migration-plan.md
  • Prefix with date for time-sensitive docs: 2025-01-14_performance-analysis.md

Required front matter:

yaml
---
created: YYYY-MM-DD
updated: YYYY-MM-DD
sessions:
  - SESSION-LOG/YYYY-MM-DD_HH-MM_session.md
status: draft | in-review | approved | superseded
tags: [planning, review, analysis]
---

5. Create Session Log

Create AGENTS/<model>/SESSION-LOG/YYYY-MM-DD_HH-MM_session-<4-6 word summary separated by hypens>.md with:

  1. Summary (2-3 sentences)
  2. Key accomplishments
  3. Decisions made
  4. Issues encountered
  5. Next session recommendations
  6. Next session prompt (copy-paste ready prompt for continuing work)
  7. Session highlights (key prompts/responses, not full transcript)

See references/session-log-format.md for template.

6. Confirm Completion

Report to user:

  • Files updated/created
  • Key changes documented
  • Recommended pickup point for next session

Directory Structure

project-root/
├── README.md
├── CHANGELOG.md
└── AGENTS/
    └── claude/
        ├── CONTEXT.md
        ├── TODO.md
        ├── DECISIONS.md
        ├── SESSION-LOG/
        │   └── YYYY-MM-DD_HH-MM_session.md
        └── PLANNING/
            └── <descriptive-name>.md

When NOT to Run

  • No meaningful work was done
  • User explicitly declines documentation
  • Project is temporary/throwaway

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