I’ve had a great experience with CLI-related skills at work. We have written CLIs for systems like Jira, along with skills that document the CLIs and describe the organisation of Jira at our company. Claude Code loads these reliably whenever you mention Jira or an issue number.

Alternatively, I’ve had less luck with purely documentation skills. They seem to be loaded less reliably when they’re not linked to actions the agent wants to take, and it is frustrating to watch the agent try to figure something out when the docs are one skill load away.