Questions

Why does my skill never trigger?

Almost always the description. Only the name and description are loaded at startup, so that one field is the entire basis on which the agent decides a task matches. A description that says what the skill is, without saying when to use it, gives the agent nothing to match against.

Write when, not just what

The specification asks the description to say what the skill does and when to use it, with keywords an agent can match against a task. Compare a description that reads as a title with one that names the trigger: file types, tool names, the words a person would use asking for the work. The second is matchable, the first is decoration.

Check the name and directory first

Before rewriting anything, confirm that the name in frontmatter matches the parent directory exactly, and that the name obeys the format: 1 to 64 characters, lowercase letters, digits and hyphens, no leading, trailing or repeated hyphens. A mismatch here produces exactly the same symptom as a bad description, which is silence.

Then look for a neighbour that already claimed the task

If two installed skills describe overlapping territory, one of them will usually win every time and the other will look broken. Narrow the descriptions until each names a distinct trigger, or merge them. This is worth checking before you conclude the format is unreliable.