Skill Debugging Assistant

A comprehensive diagnostic framework for troubleshooting skill issues by systematically analyzing triggers, parameters, prompts, and structural problems.

This skill is essential for skill developers who need to diagnose why skills aren't triggering correctly, producing unexpected behavior, or failing validation.

Skill Structure

The repository provides complete diagnostic tools and reference materials:

Main Files:

SKILL.md - Core diagnostic framework and decision trees

Resource Directories:

references/ - Detailed troubleshooting guides and templates
scripts/ - Automated validation and checking tools

Core Purpose

The Skill Debugging Assistant helps diagnose and fix four main categories of skill issues:

Skills failing to activate when expected
Incorrect or false-positive triggers firing at wrong times
Unexpected behavior despite proper triggering
Validation and packaging errors preventing deployment

Diagnostic Approach

Decision Tree Workflow

The framework uses a systematic decision tree starting with problem identification, then moves through specialized diagnostics:

Problem Identification - Categorize the specific issue type
Trigger Failure Analysis - Examine description quality and specificity
False Positive Diagnostics - Review over-broad or ambiguous descriptions
Instruction Conflict Detection - Find contradictory statements
Structure Validation - Run automated checks and manual reviews

Description Analysis

A key focus is improving skill descriptions to compete effectively among 100+ available skills:

Critical Description Elements:

Specific trigger terms - File types, task names, domains
Use-case scenarios - When and how to use the skill
Differentiating details - What makes this skill unique

Common Description Problems

Missing concrete trigger indicators
Overly broad or generic language
Lack of differentiation from similar skills
Buried critical information in references instead of main description

Key Recommendations

Trigger Optimization

Add Concrete Indicators:

File types (.tsx, .py, .md)
Task names ("code review", "data analysis")
Domain terms ("authentication", "deployment")

Replace Absolute Statements:

Change "always/never" to conditional phrasing
Use "typically", "when", "if" for nuanced triggers

Structure Guidelines

Keep SKILL.md Focused:

Under 500 lines for optimal performance
Move detailed content to references/ directory
Ensure critical instructions stay in SKILL.md
Don't bury essential information in external files

Validation Tools

The repository includes:

Python validation scripts for automated checking
YAML formatting validators
Naming convention checkers
Structural requirement analyzers

These tools catch common errors before they cause runtime issues.

Systematic Troubleshooting

The framework provides:

Quality checklists for pre-deployment review
Deep-analysis templates for complex issues
Before/after examples showing effective fixes
Common pitfall catalog with solutions

Problem Categories Deep Dive

1. Trigger Failures

When skills don't activate:

Description too generic or vague
Missing key terminology users would employ
Insufficient differentiation from other skills
Trigger words not matching user intent

2. False Positives

When skills fire incorrectly:

Over-broad descriptions
Ambiguous trigger conditions
Lack of exclusion criteria
Poor scoping of responsibilities

3. Behavior Issues

When triggered skills behave unexpectedly:

Conflicting instructions within SKILL.md
Contradictory guidance in references
Unclear precedence rules
Missing edge case handling

4. Validation Errors

Packaging and deployment problems:

YAML frontmatter syntax errors
Invalid naming conventions
Missing required fields
Structural requirement violations

Repository Resources

The repository includes complete diagnostic guides, validation scripts, troubleshooting templates, and fix examples for all common skill issues.

Visit the Skill Debugging Assistant repository for the full framework and automated tools.

About This Skill

This skill was created by Nate Jones as part of his comprehensive Nate's Substack Skills collection. Learn more about Nate's work at Nate's Newsletter.

Explore the full collection to discover all 10+ skills designed to enhance your Claude workflows!

Diagnostic framework for troubleshooting skill issues including trigger failures, false positives, unexpected behavior, and validation errors.