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

Always do both:

• Display the full prompt in a fenced code block so the user can see and manually copy it

• Copy to clipboard using pbcopy :

echo "PROMPT_CONTENT" | pbcopy # macOS

Confirm with: "Bootstrap prompt copied to clipboard (and displayed above in case you need it later)."

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)