Windows 10 Problem with Windows 10 Pro upgrades to Enterprise in Hybrid Azure AD Environment

  • Thread starter Thread starter Nick Baird
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Nick Baird

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We have a problem with some (but not all) of our Windows 10 Pro desktops upgrading to Enterprise. We have set up a domain with an on-premises Server 2016 domain controller, installed AD Connect and joined it to Azure, and so now have a hybrid set up. Everything seems to work - AD Connect reports successful syncs, and new users created on-premises appear in the Azure AD portal. Single domain, single subnet, all desktops getting group policy from the same domain controller.


We have purchased Enterprise E3 licences, and assigned them to users in the Azure AD portal.


The Microsoft instructions imply that all is required is that a user with an Enterprise licence assigned to them simply logs in to Windows 10 Pro using the synced credentials, and the Enterprise features should be automagically enabled.

This has worked for about half of our desktops, but not the other half. I can't see any obvious difference between the ones that have upgraded to Enterprise and those that haven't.


Running dsregcmd /status on the desktops reports they are AzureAdJoined and DomainJoined. Also reports "IsDeviceJoined : YES" and "IsUserAzureAD : YES".

The Azure AD portal shows all the desktops in the Devices section, and all the user logins are showing in the Azure logs, regardless of whether they have upgraded to Enterprise or not.


The Microsoft documentation for enabling Windows 10 Enterprise in a hybrid environment is very sparse, and I can't find any guides to troubleshooting the upgrade process, or forcing it. Can anyone point me in the right direction?

Thanks.....

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