Hi @JoshMartin - Two places i would ask you to check,

1. roles for which it works - role is sn_hr_core.basic   or 

2. Define availability under now assist features- Please change as per your requirement or simple choose "Skill always available" , 

3. if not working, i request you to replicate this step in your instance - https://www.servicenow.com/docs/bundle/xanadu-employee-service-management/page/product/human-resourc...

note: ensure a minimum of 200 words on the case so that generative AI can generate the resolution notes automatically.