Admin console - when adding license to user, it says assigned but actually isn't

We have an issue where we are assigning licenses (in the admin console) to users, but when they log in, it doesn't register that the license is assigned. Not on the users web portal, nor on the actual adobe app.

Strangely enough, this is only happening on new users since December 2019. We have 2x licenses assigned to users that were assigned ages ago, and they don't have any problems. It is only the 2x new users that we assigned licenses for recently that have this issue.