Office 365 license will not stay activated

Did you release Office from the previous Mac before selling/retiring/erasing it? If not, and you have a single user license, that may be the problem.

First, close all Office apps.

Login to your MS account. You must use the email address Office was purchased under.

Once in your account, in the left column, click Subscriptions. Your current subscriptions will list at the right. For 365, you may have to first click the Manage button. If you see your previous Mac listed, choose to remove it so it releases the license from that computer. Even if the correct computer is the only one listed, remove it. Logout of your account.

Restart your Mac, launch any Office app and login, again making certain to login with the email address Office was purchased under. That will create a new link to MS's server for that Mac, and should fix the issue.

The next thing I would try then is to clear the Office data in your user account, Group Containers folder.

It's been a few years now since I had Office installed, but among the several folders it creates, there are two particularly important pieces. One, all of your Outlook data is in there. Emails, contacts, etc. But more importantly for what you're trying to fix, there are files in one (or more?) of those folders that are very clearly for your activation. They're very obvious as they "license" as part of the file names or folders.

Office looks to those files and checks to be sure they match your active licenses at MS. It would be the least intrusive and easiest thing to try to find and delete those few files, then launch an Office app and try again to see if it holds.

You should contact Microsoft about this issue.

The MS 365 license is associated with your Microsoft Account and the license itself is stored deep in the MS 365 installation. It is not normally associated with the Mac Passkeys app or Keychain unless you specifically did something to do that, and even then I am not aware that it would even work that way.

There’s a Microsoft forum that’s better for issues with Microsoft 365 Copilot and its licensing issues.

Unfortunately for re-posting this over in the Microsoft forums (and for me locating the URL for the community), the Microsoft Communities website is returning this:

Longer term, two paths: migrate to LibreOffice, or the Apple iWork apps, or any of the other fine choices, or migrate to Microsoft Windows and to Microsoft 365 Copilot natively where it’ll all still have some issues but with less finger-pointing.

LibreOffice is free, and can read and write Microsoft 365 Copilot documents that earlier Office-branded versions of 365 Copilot could not.

Apple iWork apps Pages, Numbers, and Keynote are free, and can read and write native documents, and many 365 Copilot-formatted documents.

The Password app is a new interface into the authentication keychain. It is unrelated to Microsoft licensing.

Ah. That would indicate the installed apps were somehow damaged. Enough so that they weren't working as expected.

Hopefully, it holds.