We are facing constant problems with the desktop apps in O365, wheter it’s RDS servers that somehow are Azure joined by a user from login 1001 errors to modern authentication Windows that automatically disappear or other generic error 1001 logon bullshit. We have a tome of registry bullshit with shit like EnableADAL to deleting the AAD appx folder from the user profile and/or reinstalling it through Powershell and so it goes on… usually dicking around with these settings will make it magically work for a few weeks…
The amount of time this costs us and our customers is truly staggering, are we the only shop facing this?
Are you using Trend Antivirus? We just finished a months long fight of very similar symptoms, and it was that our antivirus was deleting the login tokens.
https://learn.microsoft.com/en-us/microsoft-365/troubleshoot/authentication/cannot-sign-in-microsoft-365-desktop-apps
This is what it was for us too.
No sorry, we use the same config across the board so that wouldnt explain the randomness. Ill look into it though.
We used the same config everywhere, still got randomness. Can’t explain why. Good luck!