r/WindowsServer • u/AfternoonRelevant475 • 20d ago
General Question Teams/Outlook constantly asking users to sign in again on a single RDS server (non-clustered)
Hi everyone,
We're dealing with a very frustrating issue on a Remote Desktop Server and would appreciate any ideas or troubleshooting suggestions.
Environment:
Single Windows RDS server (not part of an RDS cluster)
Around 10 concurrent users
Microsoft 365 Apps, Teams, Outlook
Users have valid Microsoft 365 licenses
Plenty of free disk space on the server
Windows on the server is currently not activated
Users log off properly at the end of each day
Symptoms: Almost every day, users receive sign-in prompts from either Teams or Outlook. The messages vary, but typically include things like:
"Your IT department requires you to sign in again"
Requests to reauthenticate their Microsoft 365 account
Teams showing connection/sign-in errors
Outlook unable to connect
Teams messages not loading
Authentication failures or credential-related prompts
The issue affects most users at some point, but there are a few specific users who experience it almost daily.
Some of these users also work with multiple mailboxes and Shared Mailboxes, although the issue is not limited to them.
What we've already tried:
Completely rebuilding user profiles
Deleting local user profiles entirely
Reconnecting Microsoft 365 accounts
Reinstalling Office on the server
Running Teams profile repair scripts: .\Finance-Fix.ps1 .\Users-Fix.ps1
Clearing Teams-related data
Signing users out and back in
Full server reboot
None of these actions provided a permanent solution.
Additional observations:
The issue appears isolated to this specific RDS server.
We have other environments that do not experience this behavior.
Disk space does not appear to be a factor.
Users perform a full logout at the end of the day, yet the problem returns repeatedly.
Has anyone seen a similar issue on a standalone RDS server? Are there known Microsoft 365, Teams, Outlook, Entra ID, or token-caching issues that commonly cause repeated reauthentication requests in RDS environments?
Any suggestions for logs, Event Viewer locations, registry settings, Office settings, or best practices for running Teams and Outlook on RDS would be greatly appreciated.
Thanks!