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Outlook 2019 needs password randomly - Office and Windows Server 2019 VDA

Dustin Kehrli




 I wanted to see if anybody has had any issues with Office 365 Outlook 2019 specially within Citrix on Windows Server 2019 authentication issues.  I have been fighting random user accounts where Outlook will randomly say "Not Connected" and "Needs Password".  Sometimes I can log them out of the application and log them back in again.  They are using shared activation on MS Office that was deployed using Microsoft Deployment Toolkit.  In some cases the password window will not show up at all until I reset the user account profile.  I have a few tickets open with Microsoft on this, but so far no progress has been made.


The environment is Citrix Cloud with Azure VMs and manually provisioned VDAs.

VDA version is 1912 CU2 LTSR with matching workspace version.

Windows Version is Server 2019 1809 (OS Build 17763.1999)

Fully patched with windows updates this week.

They don't have Azure AD connect or on prem hybrid exchange server.  This is currently in the works to be fixed.

User profile management is enabled and working correctly and setup exclusions, synchronization and mirroring from Citrix documentation.


They are running outlook in cached mode, which we have the .OST redirected to their home folder.

That made it stable enough to where they could actually log on.  We had issues with the Outlook .OST roaming with the .VHD file in the past with it unmounting correctly.

We also ran the connectivity check using Microsoft tools and testconnectivity.microsoft.com and all of those come back fine.


It appears to be something with the modern authentication on server 2019 that is causing problem or how it stores the creds?  Thoughts?


Other clients are running Server 2016 with Office 365 / Outlook 2019 without any issues.  It seems to be a windows issue at this point?

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