Earlier quoted context omitted.
I haven't had much luck with skills being called appropriately. When I have a skill called "X doer", and then I write a prompt like "Open and do X", it almost never loads up the skill. I have to rewrite the prompt as "Open and do X using the X doer skill". Which is basically exactly as much effort as what I was doing previously of having prewritten sub-prompts/agents in files and loading up the file each time I want…
Try adding a session hook that triggers on startup|resume|clear|compact to remind Claude about your custom skills.
I've mostly been working on smaller projects so I never need to compact. And skills are definitely not working even on the initial prompt of a new session.