LOW: 1-2 files, existing patterns, no new dependencies
MEDIUM: 3-5 files, minor new patterns, limited dependencies
HIGH: 6+ files, new patterns, new dependencies, cross-cutting
UNKNOWN: Cannot assess without more exploration

1. What is the task asking for?
2. What files will likely need changes?
3. What patterns exist for similar features?
4. What dependencies are involved?
5. What testing is required?

Risks to identify:
- Areas of uncertainty
- Potential blockers
- Dependencies on external factors
- Technical debt implications

estimation:
  timestamp: [ISO 8601]
  task: |
    [Task description]

  scope:
    files_affected:
      known:
        - [file1.ts - reason]
        - [file2.ts - reason]
      likely:
        - [file3.ts - reason]
      unknown: [count or "cannot determine"]

    changes_required:
      - type: [new_file | modification | deletion]
        description: [what change]
      - type: [type]
        description: [what change]

  complexity:
    overall: [low | medium | high | unknown]
    factors:
      files_to_modify: [0-3]
      new_patterns: [0-3]
      external_dependencies: [0-3]
      test_coverage: [0-3]
      documentation: [0-3]
      breaking_changes: [0-3]
      unknown_territory: [0-3]
    total_score: [sum]

  risks:
    - risk: "[Risk description]"
      likelihood: [low | medium | high]
      impact: [low | medium | high]
      mitigation: "[How to address]"

  unknowns:
    - "[What you couldn't determine]"
    - "[What needs clarification]"

  recommendations:
    approach: |
      [Recommended approach]
    alternatives:
      - "[Alternative approach 1]"
    next_steps:
      - "[First step]"
      - "[Second step]"

  confidence: 0.0
  evidence:
    - "[What you examined]"

estimation:
  timestamp: "2024-01-15T10:00:00Z"
  task: |
    Add user authentication to the existing Express API

  scope:
    files_affected:
      known:
        - src/routes/auth.ts - new route file
        - src/middleware/auth.ts - new middleware
        - src/models/user.ts - user model changes
      likely:
        - src/routes/index.ts - route registration
        - tests/auth.test.ts - new tests
      unknown: 2-3 additional files for utilities

    changes_required:
      - type: new_file
        description: Authentication routes (login, register, logout)
      - type: new_file
        description: Auth middleware for protected routes
      - type: modification
        description: Add auth to existing protected routes

  complexity:
    overall: medium
    factors:
      files_to_modify: 2
      new_patterns: 2
      external_dependencies: 2
      test_coverage: 2
      documentation: 1
      breaking_changes: 1
      unknown_territory: 1
    total_score: 11

  risks:
    - risk: "Password hashing library choice"
      likelihood: low
      impact: medium
      mitigation: "Use bcrypt, well-established"
    - risk: "JWT secret management"
      likelihood: medium
      impact: high
      mitigation: "Environment variable, document required setup"

  unknowns:
    - "Which routes should be protected?"
    - "OAuth integration needed?"
    - "Session vs JWT preference?"

  recommendations:
    approach: |
      Implement JWT-based auth with bcrypt password hashing.
      Start with login/register, add middleware, then protect routes.
    alternatives:
      - "Session-based auth with express-session"
      - "OAuth with passport.js"
    next_steps:
      - "Clarify auth requirements with user"
      - "Create detailed plan with writing-plans skill"

  confidence: 0.7
  evidence:
    - "Reviewed existing routes structure"
    - "Checked package.json for auth libraries"
    - "Examined similar features in codebase"