We have Office ProPlus 2019 VL Outlook version 16.0.10340.20017 x64 running on RDS. This is a new deployment so it's a fresh clean RDS with new profiles. Email is hosted by Office 365 and not on-prem.
Problem is Outlook started asking for password when we added another email account of the same domain. It would be OK after signing in for the entire session but upon logout and logging back in, it keeps asking for password. This only happens to users with additional account - i.e. Own email + Accounts@ or something.
I have tried all suggestions from all places in the forums - clearing Password cache, Windows Credentials, Registry key fixes and Autodiscover to no avail.
I did a test creating a new profile using the same account which works fine on its own. But when I added another account, everytime the user logs in and starts Outlook, it prompts to enter password.
2nd round of test creating a new profile using the same account. This time without adding another account but then I logged in to Office App Account - found in File > Account > User Information. This also triggered Outlook to keep prompting to enter password.
Any recommendations is much appreciated.