Enrollment Rules suddenly not working with existing groups

Not as far as I know. 

Note that if you added users to a group before you enabled the enrolment rule, those users would not be assigned. Enrolment rules only kick for those newly added to a group after you have connected the group to the rule.

https://help.docebo.com/hc/en-us/articles/360020128579-Activating-and-managing-the-Enrollment-rules-app

Could this be the issue?

Thanks for the reply, I actual opened a support ticket and apparently according to support there was a  “backlog associated with the API” and was causing a 4+ hour delay.  The situation has resolved itself, hopefully won’t happen again.

Good to know thanks ​@Matt Trigg 

Odd; I thought this was just addressed recently where they said that new limits on API would help with these types of situations. I guess there’s more work to be done.