Compact Chat

Compact Chat

Generate structured handoff documents to transfer context between chat sessions with zero ambiguity. Solves the context exhaustion problem in long-running AI coding sessions.

Mode Selection

Determine which mode applies:

COMPACT (create handoff)? User wants to save state, pause, or chat is getting long. → Follow the COMPACT flow below

RESUME (restore)? User wants to continue previous work, pasted a handoff into chat. → Follow the RESUME flow below

Proactive suggestion? After substantial work (5+ file edits, complex debugging, architecture decisions), suggest: > "We've made good progress. Want me to generate a compact to preserve context? Say 'compact' when ready."

---

COMPACT Flow

Step 1: Collect environment info

Before generating the document, collect project data:

# Branch and git status
git branch --show-current 2>/dev/null
git log --oneline -5 --no-decorate 2>/dev/null
git diff --name-only 2>/dev/null
git diff --name-only --cached 2>/dev/null
pwd

Then search for all plan/spec files in the workspace:

# Find plan files (*.plan.md, *.plan, plan-*.md, etc.)
find . -type f \( -name "*.plan.md" -o -name "*.plan" -o -name "plan-*.md" -o -name "plan.md" -o -name "*_plan_*.md" -o -name "*-plan-*.md" \) -not -path "*/node_modules/*" -not -path "*/.git/*" 2>/dev/null | sort

# Also check docs/ and common documentation folders
find . -type f -name "*.md" -path "*/docs/*" -not -path "*/node_modules/*" 2>/dev/null | sort

Important: Include ALL plan files found in the "Reference documents" section of the compact, with full absolute paths. These documents contain architecture decisions, flows, and critical context the next chat needs.

Step 2: Generate the handoff document

Using collected info + all context from the current chat, generate the document following the template below. Fill ALL sections — no placeholders. If a section doesn't apply, write "N/A" with a brief reason.

Step 3: Present to the user

Deliver the document in a copyable Markdown block. Tell the user:

1. Copy the block with Cmd+C (or Ctrl+C)
2. Open a new chat with Cmd+N
3. Paste as the first message
4. Continue where you left off

Step 4: Security check

Before delivering, mentally verify:

• [ ] No API keys, tokens, passwords, or secrets in the document
• [ ] No connection strings with credentials
• [ ] File paths are relative to the project (not absolute system paths)

If any secret is detected, remove it and warn the user.

---

Compact Template

Generate EXACTLY in this format, filled with real data from the chat:

````markdown

🔄 Compact: [descriptive task title]

Metadata

• Project: [project name or path]
• Branch: [current git branch]
• Date: [timestamp]
• Previous session: [chat link if available, or "N/A"]

Recent commits (context)

• [short hash] [commit message]
• ...

Chaining

• Continues from: [reference to previous compact, or "Initial — first compact"]
• Supersedes: [old compacts this one makes obsolete, or "None"]

---

Current State

[One paragraph describing: what was being done, where it stopped, what's working and what isn't]

What was done

• [x] [Completed task 1 — brief description]
• [x] [Completed task 2]
• ...

Decisions made

| Decision | Alternatives considered | Why this choice | |----------|------------------------|-----------------| | [Decision 1] | [Options A, B, C] | [Rationale] |

Reference documents (plans, specs, docs)

Planning and documentation files found in the project. Use absolute paths so the next chat can read them directly.

| Absolute path | What it contains | |---------------|-----------------| | /full/path/to/docs/example.plan.md | [brief description of the plan's content/purpose] |

> Note: These files are the source of truth for architecture decisions, flows, schemas, and specs. The next chat MUST read the relevant ones before continuing.

Relevant files

| File | What it is/does | Status | |------|----------------|--------| | relative/path/to/file | [description] | [modified/created/unchanged] |

Pending / Next steps

1. [ ] [Most critical action — what to do first]
2. [ ] [Second priority]
3. [ ] [Third priority]

Blockers / Open questions

• [ ] [Blocker or question — what's needed to resolve]

⚠️ Gotchas

• [Thing that can go wrong if the next chat doesn't know]
• [Non-obvious side effect, hidden dependency, etc.]

Assumptions

• [Assumption 1 that was taken as truth]
• [Assumption 2 — validate if still true when resuming]

Important context

[Any critical information that doesn't fit the categories above but the next chat NEEDS to know to continue without asking]

````

---

RESUME Flow

When the user pastes a compact into chat or asks to resume:

Step 1: Read the entire compact

Read the full document before taking any action.

Step 2: Verify current state

Run the commands below and compare with what's in the compact:

git branch --show-current
git status
git log --oneline -5

Step 3: Validation checklist

Before starting work, verify:

• [ ] Current branch matches the compact (or understand why it changed)
• [ ] Listed files still exist
• [ ] Assumptions are still valid
• [ ] Blockers have been resolved or are still pending
• [ ] Read the "Gotchas" section to avoid known pitfalls

Step 4: Assess freshness

Compare the compact's date with the current state:

• Same day, few commits: FRESH — can resume directly
• 1-2 days, some commits: SLIGHTLY STALE — review changes first
• 3+ days or many commits: STALE — consider re-exploring before continuing

Step 5: Read reference documents

If the compact contains a "Reference documents" section, read the most relevant plan files for the next pending task. These contain critical architecture context and decisions.

Step 6: Start with item #1

Begin with the first pending item in "Next steps". Reference the "Decisions made", "Reference documents", and "Gotchas" sections while working.

Step 7: Update or chain

Throughout the session:

• Mark completed items in the pending list
• If the session gets long, generate a new compact referencing this one as previous

---

Rules

1. Fill everything — the goal is that the next chat understands everything without needing to ask
2. Relative paths — use paths relative to the project for code files. Exception: reference documents (plans, specs, docs) MUST use full absolute paths so the next chat can read them directly
3. Don't include code — only file references. The new chat can read the files
4. Filter noise — ignore failed intermediate attempts and tangents. Focus on what worked and what's left
5. No secrets — never include API keys, tokens, passwords. Only environment variable names
6. Decisions with rationale — not just "chose X", but "chose X because Y and Z didn't work for this reason"
7. Gotchas are mandatory — always list at least one pitfall, even if minor. If none, write "None identified so far"
8. Copyable format — output must be a Markdown block the user copies with Cmd+C and pastes into a new chat
9. Plans are mandatory — always search and list ALL plan/spec/doc files found in the project, with absolute paths. If none found, write "No plan files found in the project"

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: douglac
• Source: douglac/compact-chat
• License: MIT

Install and usage instructions live in the source repository linked above.