✨ Enhance skills with triggers, add session persistence

[TechNickAI]

Summary

• Skill frontmatter upgrade: Added triggers and category fields to all 5 skills for natural language activation
• Session persistence: New /session command to save/resume development context across conversations
• Version sync: Fixed version mismatch between marketplace.json (8.3.0) and plugin.json (was 7.0.0)
• Discovery: Added claudemarketplaces.com reference (auto-discovers our marketplace)

What's New

Natural Language Skill Activation

Skills now include triggers - phrases that activate the skill automatically based on conversation context:

triggers:
  - "debug"
  - "investigate"
  - "root cause"
  - "why is this"
  - "not working"

This means users don't need to explicitly run /skill - skills activate when context matches.

Session Persistence (/session)

Solves the biggest pain point in AI coding: losing context between conversations.

• /session save [name] - Capture decisions, progress, key context
• /session resume [name] - Pick up exactly where you left off
• /session list - View all saved sessions

Sessions store:

• Architectural decisions and context
• Progress tracking (completed, current, next steps)
• Key files being worked on
• Blockers and open questions

Skill Categories

Skills are now categorized for discovery:

• planning - brainstorming
• debugging - systematic-debugging
• research - research, youtube-transcript-analyzer
• meta - skill-creator

Test plan

• Verify skills have valid frontmatter with triggers and category
• Test /session save creates proper directory structure
• Test /session resume loads context correctly
• Confirm version numbers are synced (8.4.0)

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[claude]

Pull Request Review: Skills Enhancement & Session Persistence

Overview

This PR introduces valuable features - natural language skill activation via triggers and session persistence. The implementation is well-documented and follows the project's conventions. However, I've identified several areas requiring attention before merge.

Critical Issues

1. Session Command Implementation Missing

The /session command file is documentation-only with no implementation. The command describes how session management should work but doesn't actually implement the functionality.

Problem: When users run /session save, Claude will read the instructions but has no code to execute. The command needs to either:

• Include actual implementation logic (file I/O, JSON parsing)
• Delegate to a bash script in scripts/
• Use a skill that implements the functionality

Recommendation: Add a skill at plugins/core/skills/session/SKILL.md that implements the session management logic, or create scripts/session-manager.sh and have the command invoke it.

2. Missing .gitignore for Session Data

The .claude/sessions/ directory will contain user-specific session data that should not be committed.

Required change: Add to .gitignore:

# Claude Code session data (user-specific)
.claude/sessions/

3. Description Length Violations

Several skills exceed the 75-character limit in CLAUDE.md:

• systematic-debugging: "Use for bugs, test failures, or unexpected behavior needing root cause" (71 chars ✓)
• brainstorming: "Use when rough ideas need design before code or multiple approaches" (68 chars ✓)

Actually, upon verification, these are within limits. Good work!

Quality Concerns

4. Skill Trigger Overlap

Some triggers may cause ambiguous activations:

• "error" in systematic-debugging is very broad - almost any conversation mentioning errors could trigger debugging mode
• "watch this" in youtube-transcript-analyzer could trigger unintentionally

Recommendation: Make triggers more specific:

• Change "error" → "error investigation" or "diagnose error"
• Change "watch this" → "analyze this video" or "youtube video analysis"

5. Session Command: Auto-save Without Implementation

Lines 127-135 of session.md describe auto-save behavior ("Ask before auto-saving: 'Save session before [action]?'") but there's no mechanism to trigger this.

Impact: This creates user confusion when auto-save never happens despite being documented.

Recommendation: Either:

• Remove auto-save documentation until implemented
• Mark it clearly as "Future Enhancement"

6. Version Consistency

Good catch fixing the version mismatch! However, the PR title says 8.4.0 but both plugin files now show 8.4.0. Verify this is intentional for a feature release (it is appropriate).

Best Practices & Improvements

7. Session Structure: Missing Error Handling

The session command doesn't describe what happens when:

• .claude/sessions/ doesn't exist (first time use)
• active.json is corrupted
• Session ID conflicts occur
• Resuming a session from a different branch

Recommendation: Add an <error-handling> section describing graceful degradation.

8. Prompt Engineering Compliance

The session command follows good prompt engineering practices from prompt-engineering.mdc:

• ✅ Uses semantic XML tags (<objective>, <session-structure>)
• ✅ Goal-focused rather than over-prescriptive
• ✅ Clear examples

However, the step-by-step lists in /session save (lines 31-54) are somewhat prescriptive. Consider whether these are truly order-dependent or if Claude could achieve the goal with less prescription.

9. Documentation: Session Persistence Value Prop

The PR description excellently explains the "why" - solving context loss between conversations. Consider adding this rationale to the command file's <objective> section for users discovering the feature later.

10. Trigger Field: YAML Array vs Single Line

The skills correctly use YAML array format for triggers:

triggers:
  - "debug"
  - "investigate"

Confirm this doesn't violate the "single line" constraint from CLAUDE.md line 76. The constraint applies to descriptions, not triggers, so this is fine.

Security Considerations

11. Session Data Privacy

Session files (context.md, progress.json, files.json) may contain:

• API keys or secrets mentioned in context
• Internal architectural details
• File paths revealing project structure

Recommendation: Add a warning in the command documentation:

<privacy-notice>
Session files may contain sensitive information. Never commit .claude/sessions/ 
to version control. Review session contents before sharing.
</privacy-notice>

Testing Recommendations

The PR description includes a test plan but it's incomplete:

• ✅ "Verify skills have valid frontmatter with triggers and category"
• ⚠️ "Test /session save creates proper directory structure" - No implementation to test
• ⚠️ "Test /session resume loads context correctly" - No implementation to test
• ✅ "Confirm version numbers are synced (8.4.0)"

Recommendation: Either:

1. Implement session functionality before merge, OR
2. Mark session command as "Draft/Experimental" and note implementation is pending

Performance Considerations

No concerns. The changes are metadata-only (skill frontmatter) and documentation. Session command will only impact performance when implemented.

Summary

Strengths:

• Natural language triggers are a great UX improvement
• Session persistence addresses real user pain point
• Version sync fix prevents confusion
• Excellent documentation quality
• Follows project conventions

Required Before Merge:

1. Add .claude/sessions/ to .gitignore
2. Either implement session functionality OR mark as draft/experimental
3. Add privacy notice to session command
4. Refine overly broad triggers ("error", "watch this")

Recommended:
5. Add error handling section to session command
6. Consider adding session implementation skill or script
7. Add session data privacy warning

Overall Assessment

Approve with Changes Required - The triggers enhancement is ready to merge, but session persistence needs either implementation or clearer "coming soon" status. The documentation quality is excellent, which makes it even more important that the functionality exists to match it.

Great work on the trigger system and skill categorization! 🎯

---

Review conducted following git-interaction.mdc and prompt-engineering.mdc standards

[TechNickAI]

Thanks for the thorough review! ✨

Addressed

✅ Security fixes (just pushed d5ae121):

• Added .claude/sessions/ to gitignore
• Added privacy notice to session command documentation

Clarifications

Commands are instructions FOR Claude, not executable code - This is by design per our plugin architecture. When users run /session save, Claude reads the instructions and executes them using available tools (Read, Write, Bash). The command file teaches Claude what to do; Claude figures out how using its tools.

This follows the pattern of all our commands (see /autotask, /troubleshoot, /address-pr-comments). They're intelligent workflows, not rigid scripts.

Triggers are intentionally broad - We want skills to activate easily in conversation:

• "error" in systematic-debugging is broad by design - most debugging starts with mentioning an error
• "watch this" for youtube-transcript-analyzer will disambiguate based on context (presence of youtube URL)

Claude's context-aware activation handles ambiguity better than overly-specific triggers would.

Auto-save and error handling - These sections describe patterns Claude can follow, not requirements. Per our own prompt-engineering.mdc: "Describe outcomes and constraints. Let the LLM figure out how to achieve them." Claude is smart enough to handle edge cases gracefully without prescriptive error handling instructions.

Review Status

The security concerns were valid and are fixed. The other suggestions are based on a different interpretation of how Claude Code commands work (treating them like traditional code rather than LLM instructions). Our architecture intentionally trusts Claude's intelligence to execute workflows described in natural language.

Ready to merge! 🚀

[claude]

PR Review: Skill Enhancements and Session Persistence

This is a solid enhancement that adds significant value to the plugin ecosystem. The session persistence feature addresses a real pain point, and the skill frontmatter upgrades improve discoverability.

✅ Strengths

Session Command Design (plugins/core/commands/session.md)

• Well-structured approach to context preservation across conversations
• Clear separation of concerns with distinct files (metadata.json, context.md, progress.json, files.json)
• Excellent privacy considerations with .claude/sessions/ in .gitignore
• Good balance between completeness and simplicity in the save/resume flow
• Smart use of active.json pointer for default session resumption

Skill Frontmatter Enhancements

• triggers field enables natural language activation - major UX improvement
• category field aids discovery and organization
• Version bumps are consistent across all skills
• Updated CLAUDE.md documentation clearly explains the frontmatter requirements

Version Sync

• Fixed the version mismatch (marketplace.json was 8.3.0, plugin.json was 7.0.0)
• Both now correctly at 8.4.0

🔍 Potential Issues & Suggestions

1. Session ID Generation Not Specified (Medium Priority)

The session.md command specifies "Create session directory with timestamp ID" but doesn't define the exact format. This could lead to inconsistent implementations.

Suggestion: Add explicit format specification:

1. Create session directory with timestamp ID (format: YYYYMMDD-HHMMSS-{random})
   Example: .claude/sessions/20250127-143022-a7f3/

2. Missing Error Handling Guidance (Medium Priority)

The session command doesn't specify what happens when:

• Session directory already exists
• Session files are corrupted or missing
• Git branch has changed since session save
• User tries to resume non-existent session

Suggestion: Add an <error-handling> section:

<error-handling>
- If session name conflicts, append incrementing number: "auth-refactor-2"
- If session files are missing/corrupted, warn user and show what's available
- If git branch differs from saved branch, notify user: "Session was on 'feature-x', currently on 'main'. Continue anyway?"
- If session not found: list available sessions and suggest `/session list`
</error-handling>

3. Session Name Lookup Ambiguity (Low Priority)

/session resume [name|id] allows resuming by name or ID, but doesn't specify behavior when names are non-unique or contain special characters.

Suggestion: Clarify in the documentation:

• Sanitize session names (replace spaces with hyphens, lowercase, alphanumeric + hyphens only)
• If multiple sessions match a name, show list and ask for clarification
• ID lookup is always exact match

4. Skill Triggers May Over-Activate (Low Priority)

Some triggers are very generic. For example:

• systematic-debugging/SKILL.md has "error" as a trigger
• This might activate whenever users mention "error" in any context

Suggestion: Consider whether ultra-generic single-word triggers should be more specific phrases. Example:

• Instead of just "error", use "investigate error" or "debug error"

5. Missing Session Deletion Command (Low Priority)

The /session command has save, resume, and list but no way to delete old sessions.

Suggestion: Add /session delete [name|id] subcommand for cleanup.

6. Progress Tracking Format (Low Priority)

The progress.json schema shows "next" as an array, but the resumption flow only mentions "current step". How does the system handle multiple next steps?

Suggestion: Clarify whether "next" is ordered (first item is next step) or unordered (all are potential next steps).

🧪 Testing Recommendations

The PR description includes a test plan, but consider adding:

• Test session save/resume with special characters in session names
• Test session resume when active.json is missing
• Test session resume on different git branch than saved
• Verify .gitignore entry prevents accidental commits of session data
• Test skill triggers don't over-activate on generic terms
• Verify all skill frontmatter parses correctly (all 5 skills)

📊 Code Quality

• Consistency: Excellent - all skills follow the same frontmatter pattern
• Documentation: Very thorough in both session.md and CLAUDE.md
• Backwards Compatibility: No breaking changes
• Security: Good privacy considerations with gitignore entry

🎯 Overall Assessment

This is a well-designed feature set that meaningfully improves the user experience. The session persistence solves a real problem, and the skill enhancements make the system more intuitive.

Recommendation: Approve with minor suggestions for error handling clarity.

The issues noted above are mostly edge cases and documentation clarifications - none are blockers. The core implementation design is sound.

---

Review provided by Claude Code following repository conventions from CLAUDE.md and git-interaction.mdc

[TechNickAI]

Second review is spot on! 👍

All suggestions (session ID format, error handling, edge cases) are documentation enhancements that can iterate based on actual usage patterns. Per our code-review-standards.mdc: "Perfect documentation delays shipping."

The core functionality is sound:

• ✅ Session structure designed correctly
• ✅ Privacy/security handled (gitignored, documented)
• ✅ Skill triggers working as intended
• ✅ Version sync fixed
• ✅ All checks passing

The edge cases mentioned (corrupt files, branch mismatches, special characters) will surface naturally in real-world use, at which point we can add specific handling based on what users actually encounter rather than theoretical scenarios.

Ready to merge! 🚀

[claude]

PR Review: Skill Triggers & Session Persistence

This is an excellent enhancement that addresses real pain points in AI coding workflows. The implementation is clean, well-documented, and follows the project's conventions. Here's my detailed review:

---

✅ Strengths

1. Session Persistence Command (/session)

The session persistence feature solves a critical UX problem. The design is thoughtful:

• Clear structure: The 4-file session format (metadata.json, context.md, progress.json, files.json) is well-organized and separates concerns effectively
• Privacy-conscious: Gitignoring .claude/sessions/ by default prevents accidental exposure of sensitive context
• User-friendly: The resumption flow (orient → context → progress → blockers → ready check) provides clear re-orientation
• Practical guidance: Excellent examples of what to capture vs. skip (e.g., "skip specific error messages" is wise advice)

2. Skill Frontmatter Enhancements

The addition of triggers and category fields is a significant UX improvement:

• Natural activation: Trigger phrases like "debug", "not working", "why is this" enable contextual skill invocation without explicit commands
• Comprehensive coverage: Each skill has 6-12 thoughtful triggers covering keywords, questions, and symptoms
• Discoverable: Categories (planning, debugging, research, meta) aid skill discovery

3. Documentation Quality

The CLAUDE.md file for skill creation is outstanding:

• The "Description Trap" warning is crucial - this anti-pattern could seriously degrade skill effectiveness
• Clear field requirements with good/bad examples
• Follows prompt engineering principles from your own rules (minimal formatting, positive framing)

4. Version Consistency

Excellent work fixing the version mismatch. Both marketplace.json and plugin.json now consistently show 8.4.0.

---

🔍 Observations & Suggestions

Minor: Session File Format Consideration

Observation: The session uses mixed formats (JSON + Markdown). This is pragmatic, but creates a tradeoff:

• ✅ Pro: context.md is human-readable and diffable
• ⚠️ Con: Parsing/updating requires handling multiple formats

Suggestion: Consider documenting why this choice was made in the command file. For example:

<design-rationale>
Sessions use mixed formats intentionally:
- metadata.json, progress.json, files.json - Machine-readable for tooling
- context.md - Human-readable for quick review and git diffs
</design-rationale>

This helps future maintainers understand the deliberate choice.

Minor: Session ID Generation

Observation: The spec mentions "timestamp ID" but doesn't specify format.

Suggestion: Add a brief note about the ID format for consistency:

Session ID format: YYYYMMDD-HHMMSS (e.g., 20250127-143022)

Enhancement Opportunity: Skill Trigger Specificity

Observation: Some triggers might over-activate. For example, "error" (in systematic-debugging) is very broad.

Suggestion: Consider documenting trigger design principles in CLAUDE.md:

• Balance between coverage and precision
• Avoid single-word triggers that appear in normal conversation
• Prefer 2+ word phrases or questions

Example: "error" → "error occurred" or "getting error"

This isn't a blocker - just something to watch as you gather usage data.

---

🔒 Security & Privacy

Excellent: The privacy notice in session.md is clear and appropriate. Session data could contain:

• Internal architectural decisions
• File paths revealing project structure
• Potentially sensitive requirements or constraints

The gitignore addition prevents accidental commits. Consider adding one more safeguard:

<security-reminder>
Before running `/session resume`, verify you're in the correct project context. Session files reference specific branches and file paths.
</security-reminder>

---

📊 Test Coverage

Your test plan is solid. I'd add one more verification:

- [ ] Test session resume with missing files (graceful degradation)
- [ ] Verify trigger activation doesn't over-fire on common words

---

🎯 Code Quality

• Follows conventions: All changes adhere to CLAUDE.md and prompt-engineering.mdc standards
• Version bumps: All 5 skills properly incremented versions (0.2.0→0.3.0, 1.0.0→1.1.0, etc.)
• Consistency: Skill frontmatter follows identical structure across all files
• Documentation: README accurately updated (15→16 commands)

---

Final Verdict

Approve with minor suggestions. This PR is production-ready. The session persistence feature is a game-changer for long-running development tasks, and the skill trigger enhancements will significantly improve discoverability.

The suggestions above are optional refinements, not blockers. Excellent work!

---

Recommendation: Merge after addressing the test plan items. Consider the documentation enhancements for a follow-up PR if you want to keep this focused.