Office 2019 not authenticating to o365 on Server 2019 RDS servers RRS feed

  • Question

  • Hello,

    We have had to re-create a client's servers recently do to unforeseen issues.  They have a RDS set of servers that are managed by a RD Gateway broker.  We have setup FSLogix to allow for seamless moving of users between the 2 RDS servers with all settings and customer experiences moving with them.  We had it all working for about a month in production and we started getting a call from 2 clients (only 2 out of 20 so far) that when they are on a specific server, Office 2019 apps will not authenticate nor will Outlook sign into o365 exchange for them to get mail.  Have them log out and force them to the other RDS server and everything works normally.  I have been banging my head over this and have not been able to find anything in the FSLogix logs nor any of the windows event logs and points to anything.  And the issue isn't on the same server for both users, but getting them working by having them force to the one specific server has worked.  I setup a remote desktop connection direct to the specific servers for each user to get around this.  

    Thank you,



    Saturday, July 25, 2020 4:28 AM

All replies

  • Naturally, the options outlined above are not completely satisfying for customers looking to combine cloud technologies with a modern server infrastructure in a hybrid environment.
    The good news: There is another way of combining Office 365 ProPlus with Windows Server 2019. But it takes some adaptability – i.e. a workaround – that is again secluded away in the system requirements for Office 365 ProPlus.

    While Windows Server 2019 is missing, the requirements do list the Windows operating system in a number of versions. So although it is not possible to virtualize Office 365 ProPlus directly on Windows Server 2019, there is certainly the option of using Windows Server 2019 to provision the Windows operating system – which in turn would support Office 365 ProPlus.

    This means that Office 365 ProPlus can be combined with Windows Server 2019 by switching from a virtualized, remote application to a virtual desktop with a VDI environment.

    The Azure service Windows Virtual Desktop – which will likely be available from 2019 – is another option, for the future at least. Put simply, it is a remote virtual desktop environment for Windows and Office that is made available as a managed service in Azure. Besides the benefits of a cloud service, it comes with another exciting feature, the Multi-User Windows 10 Experience that allows several users to ‘share’ one virtual desktop. Windows Virtual Desktop is optimized specifically to run with Office 365 ProPlus, which means that this service can also be used to provide a virtualized form of Office 365 ProPlus – albeit in the Microsoft Cloud.

    Watch out for licensing traps
    All of the provisioning options outlined above have technical and licensing consequences.

    For instance, virtualization of Office 365 ProPlus within a virtual desktop requires not only an Office 365 ProPlus license and a RDS CAL, but also a Windows or VDA license – either with an active SA or an active subscription. Interested parties should exercise particular caution when dealing with licenses purchased via CSP, as the licenses that are available in this program only permit virtualization of the operating system on servers hosted in Azure.

    A disadvantage currently associated with Windows Virtual Desktop is that the service is only available with Windows Enterprise licenses. At present, Windows Virtual Desktop does not have a solution for thin clients – which based on the momentary license conditions are only equipped with a VDA license. But the licensing requirements might certainly change, as the service will not be available until 2019.

    It is certainly not compliant to provision Office 2019 on the server instead of Office 365 ProPlus – at least without purchasing Office on-premises licenses. It is essential to be particularly careful if the Microsoft 365 From SA license was purchased. Although it currently gives users access to Office Professional Plus, it only does so as a local copy for the licensed user – which means that provisioning on a terminal server is not compliant with the licensing terms.

    So everyone currently planning a virtual rollout of Microsoft Office on Windows Server 2019 while keeping the option open to use Office 365 ProPlus would be well advised to remember the option of add-on licenses. They offer full rights of use for Office 2019 on-premises, with provisioning on terminal servers, as well as the right to provision Office 365 ProPlus. This ensures fully compliant use of all technical options associated with the virtualization of Windows Server 2019 in combination with Office.
    Saturday, July 25, 2020 11:34 AM
  • OK.  We decided to clear one of the users FSLogix profile vhd's and have them log back in to re-create them.  So far the end user is reporting that all is good on.  And the servers logs indicate she has been on both the 2 terminal servers.  Just need to do the same to the other user affected. :D


    Wednesday, July 29, 2020 10:51 PM
  • Hi

    We had the same problem and we had some sleepless nights until we set the two registry keys mentioned here for example:

    Originally I had another website pointing to the registry keys, but can't find that anymore.

    The bigges PITA was, that the error somethings happened and then for days all worked ok till it came back again.



    Friday, August 7, 2020 4:27 PM