Add Checkpoints to a Skill

Analyze a skill and generate appropriate checkpoints.yaml for the automated-assessment framework.

Command

/add-checkpoints                    # Analyze current skill directory
/add-checkpoints typo3-docs         # Analyze a specific installed skill
/add-checkpoints --dry-run          # Show what would be generated, don't write

Workflow

1. Locate the skill — find SKILL.md, references/, scripts/, assets/
2. Analyze suitability — determine if checkpoints make sense (see criteria below)
3. Extract requirements — parse SKILL.md for verifiable rules and patterns
4. Generate checkpoints — create checkpoints.yaml with mechanical checks and LLM reviews
5. Add preconditions — determine which project types this skill applies to
6. Validate — run scripts/run-checkpoints.sh against a sample project to verify
7. Report — explain what was generated and why, or why checkpoints don't fit

Suitability Criteria

A skill is suitable for checkpoints if it defines:

• File structure requirements (directories, config files, manifests)
• Content patterns (must contain X, must not contain Y)
• Naming conventions (prefixes, suffixes, case rules)
• Tool configurations (PHPStan level, linter rules, CI steps)
• Metadata standards (license, author, version format)

A skill is NOT suitable if it only provides:

• Conceptual guidance without verifiable outputs
• Interactive workflows with no persistent artifacts
• Runtime behavior patterns (performance, caching strategies)

Report suitability with reasoning so the user can decide.

Checkpoint Generation Rules

Mechanical Checks

Extract from SKILL.md patterns like:

• "must exist" / "required" → file_exists
• "must not" / "never" / "avoid" → file_not_exists or not_contains
• "must contain" / "should have" → contains or regex
• Version/format constraints → json_path or command

Preconditions

Derive from the skill's scope:

• TYPO3 extensions → file_exists: ext_emconf.php
• Docker projects → file_exists: Dockerfile
• Go projects → file_exists: go.mod
• Skill repos → file_exists: .claude-plugin/plugin.json
• Universal (any project) → no preconditions

ID Convention

Use the skill's established prefix from references/migration-guide.md, or derive a 2-letter prefix from the skill name.

Severity Assignment

• error: "must", "required", "never" → blocks release
• warning: "should", "recommended" → suggestion
• info: "consider", "nice to have" → optional

LLM Reviews

For subjective requirements that can't be mechanically verified:

• Code quality judgments → domain: code-quality
• Documentation completeness → domain: documentation
• Architecture decisions → domain: architecture

Group by domain, provide clear rubric prompts.

Output

Generates checkpoints.yaml in the skill's directory following the schema at references/checkpoints-schema.md. Also creates a copy in the automated-assessment assets directory.

References

• Schema: references/checkpoints-schema.md
• Migration guide: references/migration-guide.md
• Existing checkpoints: assets/*-checkpoints.yaml (as examples)