Productivity

dev-session - Claude MCP Skill

Manage long development sessions with structured progress tracking. Creates SESSION.md files for multi-session handoff, checkpoints progress with WIP commits, and captures learnings to CLAUDE.md. Trigger with 'start session', 'checkpoint', 'wrap session', 'resume session', or 'context getting full'.

SEO Guide: Enhance your AI agent with the dev-session tool. This Model Context Protocol (MCP) server allows Claude Desktop and other LLMs to manage long development sessions with structured progress tracking. creates session.md files for mul... Download and configure this skill to unlock new capabilities for your AI workflow.

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SKILL.md
# Dev Session

Manage multi-session development work with structured progress files, checkpoint commits, and durable learnings. Produces SESSION.md files that survive context compaction and enable clean handoff between sessions.

## Operating Modes

### Mode 1: Start Session

**When**: Beginning multi-step work, "start session", "new session for [feature]"

1. Check if `SESSION.md` already exists in the project root
   - If yes: read it and ask whether to **continue** the existing session or **start fresh**
   - If no: create from template (see [references/session-template.md](references/session-template.md))
2. Pre-fill fields:
   - **Project**: from CLAUDE.md or directory name
   - **Branch**: from `git branch --show-current`
   - **Last Updated**: current timestamp
   - **Phase**: ask user what they're working on
3. Read the project's CLAUDE.md to orient on context
4. Present a brief summary: "Session started. Working on [phase] on branch [branch]."

### Mode 2: Checkpoint

**When**: "checkpoint", major milestone reached, before risky changes, context getting large

1. Update SESSION.md:
   - Add completed items to **What Works**
   - Update **Current Position** with exact location (file paths, line numbers)
   - Clear resolved **Blockers**, add new ones
   - Write concrete **Resume Instructions**
2. Capture learnings:
   - If any patterns, gotchas, or commands were discovered during work, add them to CLAUDE.md
   - One line per concept — concise, not verbose
3. Git checkpoint:
   ```bash
   git add -A && git commit -m "WIP: [what was accomplished]"
   ```
4. Record the commit hash in SESSION.md under **Checkpoint**
5. Confirm: "Checkpointed at [hash]. SESSION.md updated."

### Mode 3: Resume Session

**When**: "resume", "continue from last session", "where were we", start of a new conversation

1. Read `SESSION.md` — if missing, inform user and offer to start a new session
2. Read the project's `CLAUDE.md` for context
3. Check what's changed since the recorded checkpoint:
   ```bash
   git log --oneline [checkpoint-hash]..HEAD
   ```
4. Check for uncommitted changes: `git status`
5. Present a summary:
   - **Phase**: what we were working on
   - **Position**: where we left off
   - **Changes since**: any commits or modifications since checkpoint
   - **Blockers**: anything unresolved
   - **Suggested next step**: first item from Resume Instructions

### Mode 4: Wrap Session

**When**: "wrap session", "done for now", "save progress", ending a session

1. Run a full checkpoint (Mode 2)
2. Review SESSION.md for completeness:
   - Are Resume Instructions concrete enough for a fresh session to continue?
   - Is Current Position specific (file paths, not vague descriptions)?
3. If the phase is complete:
   - Collapse the phase summary to 2-3 lines
   - Clear Resume Instructions or note "Phase complete — ready for next phase"
4. Confirm: "Session wrapped. Resume with 'resume session' next time."

## When to Use

| Scenario | Use this skill? |
|----------|----------------|
| Multi-phase feature spanning 2+ sessions | Yes |
| Work that might hit context compaction | Yes |
| Before making risky or destructive changes | Yes (checkpoint first) |
| Quick bug fix or single-file edit | No |
| Single-session task with clear scope | No |

## SESSION.md Principles

- **Track progress, not architecture** — SESSION.md is a work log, not project documentation
- **Concrete over vague** — "Resume at `src/auth.ts:42`, implement token refresh" beats "Continue auth work"
- **Collapse completed work** — finished phases become 1-2 line summaries
- **Keep under 100 lines** — if it's longer, collapse more aggressively

## Autonomy Rules

- **Just do it**: Read SESSION.md, read CLAUDE.md, check git status/log, present summaries
- **Brief confirmation**: Creating new SESSION.md, committing WIP checkpoints
- **Ask first**: Overwriting an existing SESSION.md, deleting session data

## Reference Files

| When | Read |
|------|------|
| Creating a new SESSION.md | [references/session-template.md](references/session-template.md) |
| Context compaction tips, what survives | [references/compaction-survival.md](references/compaction-survival.md) |

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Information

Repository
jezweb/claude-skills
Author
jezweb
Last Sync
2/21/2026
Repo Updated
2/20/2026
Created
2/18/2026

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