Sometimes Windows’ relationship with 365, or a user’s profile, or just a user on a PC or terminal server, will not log into 365. This appears to be the result of corruption of cached credentials.
The most straightforward way is probably to nuke all User/Windows/Azure relationship and recreate. As written, this would probably be very bad on a terminal server, because it will nuke the relationship for all users and all profiles. So far, no per-user commands identified.:
Remove 365 accounts from “Access Work and School”, then run these:
dsregcmd /debug /cleanupaccounts
dsregcmd /debug /leave
from administrative CMD, and also from SYSTEM (paexec or psexec can do this), then reboot, then remove from Access Work and School if still there, then set up user relationship(s) again.
But today we have a report that dsregcmd /status did something, unknown, which fixed one terminal server user. Not sure what. Next time I plan to run many tests with this info:
And if you see error CAA5021, do this:
Search for Manage user certificates in the search bar and open it from Best match. Then navigate to Current User\Personal\Certificates and make sure the MS-Organization-Access and MS-Organization-P2P-Access entries are deleted.
No reboot needed for that last.