I previously assigned Microsoft 365 licenses manually to users, but I'm looking to simplify the process by switching to group assignments. The problem I'm encountering is that when there aren't enough available licenses to cover the transition, I get an error message saying, 'You don't have enough licenses to assign to everyone selected. Buy more licenses or remove some users or groups to continue.'
For example, I have 100 users who are assigned an E3 license manually, and I bought a total of 105 E3 licenses, meaning I have 5 licenses available. However, when I add those 100 users to an 'E3 Licensed' group and try to apply the group assignment, it seems as if the system is attempting to license all 200 users instead of the 100.
What would be the best way to add the group without removing the current manual assignments? I'm concerned that if I remove the manual licenses and the users aren't part of a group assignment yet, they could lose access to various services, like soft deleted mailboxes and other functionalities. Any advice would be appreciated!
4 Answers
Unfortunately, there's no way to add them without removing the manual assignments first. But you can streamline the process with PowerShell; just remove the current licenses and then add the users to the group. It can all be done in about 30 seconds!
The best way to handle this is to delicense everyone first, then apply the group assignment. Just keep in mind that there might be a brief period where users are without licenses, but it shouldn't cause major issues—better to inform your users about it as a maintenance window.
Have you considered adding the users in smaller batches, like 5 at a time? It could help avoid the error message you're seeing. You might even be able to automate the process to make it faster.
Just a heads up, there's actually a grace period of 30 days on reassigning licenses. So, it's definitely advisable to remove the directly assigned licenses first, then add the users to the group afterward.

Absolutely, this approach works great! Just remember, if you're switching from one license type to another, like from E3 to E5, you need to remove the old license before adding the new one. Adding first can mess things up, and might even deactivate the mailbox.