debrief

Session Debrief

Capture learnings from the current session and persist them into project documentation. The goal is continuous improvement: never repeat the same mistakes, always build on what we learn.

Phase 1: Review the Session

Scan the conversation history for learnings. Look for these signals:

Signal	What to capture
Corrections ("no, use X instead")	The right approach and why the wrong one fails
Debugging breakthroughs	Root cause and fix, not just the symptom
Repeated mistakes	Pattern that keeps tripping us up
Architectural decisions	What was chosen and the reasoning
Surprising behavior	Gotchas, edge cases, unintuitive APIs
Process friction	Steps that were slow, confusing, or error-prone
Discovered conventions	Patterns in the codebase that weren't documented

Categorize each learning:

Category	Typical destination
Mistake/Correction	CLAUDE.md (universal) or .claude/rules/ (domain-specific)
Architectural Decision	CLAUDE.md or project docs (ARCHITECTURE.md, ADRs)
Gotcha/Pitfall	.claude/rules/ with path-scoping
Pattern/Convention	.claude/rules/ with path-scoping
Process Improvement	CLAUDE.md or CONTRIBUTING.md
Debugging Insight	.claude/rules/ topic file

If the session had no meaningful learnings (simple task, everything went smoothly), say so and stop. Don't force learnings that aren't there.

Phase 2: Audit Existing Documentation

Before proposing changes, read CLAUDE.md, scan .claude/rules/ for existing rule files, and check for project docs (ARCHITECTURE.md, CONTRIBUTING.md, docs/). Follow any @ imports and path references in CLAUDE.md to discover documentation locations.

For each learning, check:

• Is it already documented? → Skip
• Does it contradict existing docs? → Propose update to existing entry
• Is it genuinely new? → Propose addition

Estimate CLAUDE.md line count and track against the 300-line budget.

Phase 2.5: Prune Stale Entries

Activates when BOTH conditions are true:

• CLAUDE.md is above 250 lines
• Phase 1 found high-signal learnings that warrant CLAUDE.md addition

Scan CLAUDE.md for entries that no longer earn their place:

Category	How to verify
Duplicated by docs	Entry restates guidance in a docs/*.md file that CLAUDE.md already references
Enforced by toolchain	Linter, ast-grep, CI, or pre-commit hook already catches this (check config files)
Outdated	Convention no longer matches codebase (verify with grep/glob)
Session debris	Ephemeral context from a past session that was never cleaned up

Rules:

• Require evidence for every removal — cite the doc, linter rule, or grep result that proves staleness
• When uncertain, keep the entry — false removals are worse than bloat
• Never prune architectural decisions or safety-critical rules without explicit user confirmation
• Present removals in Phase 3 alongside additions so the user sees the full picture

Phase 3: Propose Updates

Present ALL proposed changes to the user in a single summary before writing anything.

Format for Proposals

## Session Debrief: Proposed Updates

### 1. CLAUDE.md (289 → 285 lines, net -4)
**Removals (pruned):**
- **Remove line 142**: "Use X pattern" — now documented in docs/SERVICES.md (referenced on line 12)
- **Remove line 87**: "Run prettier before committing" — enforced by pre-commit hook in .husky/pre-commit

**Additions:**
- **Add**: "IExceptionHandler gotcha: need both AddExceptionHandler() and UseExceptionHandler() (see src/Program.cs:42)"
- **Update**: Change "Use npm" → "Use pnpm (npm causes lockfile conflicts)"

### 2. .claude/rules/api-conventions.md (new file)
- **Add**: Path-scoped rule for `src/api/**/*.ts`
- Content: "All API handlers must validate input with zod schemas before processing"

### 3. Skipped
- [Session-specific detail] — not generalizable
- [Already documented in .claude/rules/testing.md]

CLAUDE.md Token Discipline

These rules are non-negotiable when proposing CLAUDE.md changes:

1. Under 300 lines — If above 250, trigger Phase 2.5 pruning before routing to .claude/rules/
2. Earn its place — Ask: "Would removing this cause Claude to make mistakes in future sessions?" If no, don't add it.
3. One-liners only — Brief, actionable. No paragraphs.
4. No inline code blocks — Use file:line references (e.g., see src/config.ts:15-20)
5. Use @imports for detailed docs — @docs/api-patterns.md not inline explanations
6. Route domain knowledge to .claude/rules/ — Path-scope when possible
7. Prefer updating over adding — Extend an existing bullet point rather than adding a new one
8. Never duplicate linter rules — If ESLint/Prettier/Ruff enforces it, don't document it

.claude/rules/ Best Practices

• One topic per file — api-conventions.md, testing.md, debugging.md
• Use path-scoping when the rule only applies to certain files
• Keep files focused — 20-50 lines per file, not sprawling documents
• Use clear filenames — Future sessions need to find these by name

Project Docs Updates

When updating CONTRIBUTING.md, ARCHITECTURE.md, docs/*.md:

• Check for a docs/ folder and route learnings to the most specific existing doc
• Follow CLAUDE.md @ references to find authoritative locations
• Match existing style, add to existing sections
• Keep it useful for humans too — these docs serve the whole team

Phase 4: Apply with Approval

Use AskUserQuestion to get approval:

{
  "questions": [{
    "question": "Here are the proposed documentation updates from this session. Which should I apply?",
    "header": "Updates",
    "multiSelect": false,
    "options": [
      { "label": "Apply all", "description": "Apply all proposed changes listed above" },
      { "label": "CLAUDE.md only", "description": "Only update CLAUDE.md, skip other files" },
      { "label": "Rules only", "description": "Only update .claude/rules/ files" },
      { "label": "Let me pick", "description": "Show each change individually for approval" }
    ]
  }]
}

After applying, show a summary table of what was updated with file, change description, and line delta. Report final CLAUDE.md line count and remaining budget.

What NOT to Capture

• Session-specific context — "We were debugging issue #42" (ephemeral)
• Speculative conclusions — "This might also affect X" (unverified)
• Obvious things — "Use git to commit" (Claude already knows)
• Temporary workarounds — Unless they're long-lived and affect the team
• Personal preferences — Route to ~/.claude/CLAUDE.md or CLAUDE.local.md instead
• Things the linter catches — Trust the toolchain

Edge Cases

• No CLAUDE.md exists: Create a minimal one with the project name and the first learning
• CLAUDE.md above 250 lines: Trigger Phase 2.5 pruning first. Only fall back to routing all learnings to .claude/rules/ if pruning cannot free sufficient space
• .claude/rules/ doesn't exist: Create it with the first rule file
• Contradictory information: Flag explicitly. Don't silently overwrite — the existing docs may be correct
• No learnings found: Say so honestly. Don't manufacture learnings to justify running the skill

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