This is kinda complicated, but the Mac is not checking in every 15 minutes. In fact, it hasn't checked in since Mid-December, but a few management commands have run.
Is there a way to remote force a check in without removing in and running the sudo command? It would seemingly have to be a configuration policy? Since it is only one user, I should be able (if responsive) to remote in and run it the terminal, but if the user isn't responsive, I still want it to check in since there have been updates that need to be installed.