Licenses assigned through admin console not working

Since a couple of days it appears licenses I'm assigning through the admin console are no longer actually being received by users.

On the admin console end everything looks fine. I can add a user, assign a product to them, it will show the user as a member of that product group, and my available licenses decrease by one.

But the users never receive any email from adobe telling them they've received the license, and when they log in to their creative cloud page it still appears like they have no active subscriptions. It only shows the free apps as available. 

I've tried it on my own account. Added a license, removed a license, added the license again, and it doesn't seem to make any difference.

Any idea what's going on and how I can troubleshoot this?