session-handoff

name

session-handoff

description

Generate a smart bootstrap prompt to continue the current conversation in a fresh session. Use when (1) approaching context limits, (2) user says "handoff", "bootstrap", "continue later", "save session", or similar, (3) before closing a session with unfinished work, (4) user wants to resume in a different environment. Outputs a clipboard-ready prompt capturing essential context while minimizing tokens.

Session Handoff

Generate a bootstrap prompt that enables seamless conversation continuity in a new session.

Process

1. Analyze Current Session

Identify and categorize:

• Goal state: What is the user trying to accomplish? What's the end state?
• Current progress: What's been done? What's working?
• Blockers/open questions: What's unresolved? What decisions are pending?
• Key artifacts: Files modified, commands run, errors encountered
• Critical context: Domain knowledge, constraints, or preferences established

2. Apply Token Efficiency Heuristics

Include:

• Specific file paths, function names, error messages (hard to rediscover)
• Decisions made and their rationale (prevents re-discussion)
• Current hypothesis or approach being tested
• Exact reproduction steps for bugs

Exclude:

• General knowledge Claude already has
• Verbose explanations of standard concepts
• Full file contents (use paths + line numbers instead)
• Conversation pleasantries or meta-discussion

Compress:

• Use bullet points over prose
• Reference files by path, not content
• Summarize long error traces to key lines
• Use "established: X" for agreed-upon decisions

3. Structure the Bootstrap Prompt

## Context
[1-2 sentence goal statement]

## Progress
- [Completed item with outcome]
- [Completed item with outcome]

## Current State
[What's happening right now - the exact point to resume from]

## Key Files
- `path/to/file.ext` - [role/status]

## Open Items
- [ ] [Next immediate action]
- [ ] [Subsequent action]

## Constraints/Decisions
- [Established constraint or decision]

4. Output

Copy the bootstrap prompt to clipboard using:

echo "PROMPT_CONTENT" | pbcopy  # macOS

Confirm with: "Bootstrap prompt copied to clipboard. Paste it to start a new session."

Adaptive Sizing

Simple tasks (bug fix, small feature): 100-200 tokens

• Goal, current file, error/behavior, next step

Medium tasks (feature implementation, refactor): 200-400 tokens

• Goal, progress list, current state, key files, next steps

Complex tasks (architecture, multi-system): 400-800 tokens

• Full structure above, plus constraints and decision rationale

Example Output

## Context
Adding OAuth login to the Express app, Google provider first.

## Progress
- Installed passport, passport-google-oauth20
- Created `src/auth/google.ts` with strategy config
- Added `/auth/google` and `/auth/google/callback` routes

## Current State
Callback route returns "Failed to serialize user into session" - need to implement serializeUser/deserializeUser in passport config.

## Key Files
- `src/auth/google.ts` - strategy setup (working)
- `src/routes/auth.ts:45` - callback handler (error here)
- `src/app.ts` - passport.initialize() added, missing session serialize

## Open Items
- [ ] Add serialize/deserialize to passport config
- [ ] Test full OAuth flow
- [ ] Add session persistence (currently memory store)

## Constraints
- Using express-session with default memory store for now
- Google OAuth credentials in .env (GOOGLE_CLIENT_ID, GOOGLE_CLIENT_SECRET)