Microsoft 365 E5 - Windows 10 subscription activation for hybrid Azure AD joined devices

Brass Contributor

We have On Premises AD synced to Office365 (Azure) and Users having "Microsoft 365 E5" Licences.

Dell Desktops with Windows 10 PRO 1803 version joined to On-Premises AD and they are Activated to Windows PRO. Also Windows 10 Machines are showing in Azure AD Portal with "Hybrid Azure AD joined" and dsregcmd /status shows AzureAdJoined : YES.


But Machines are not getting upgraded from PROD to Enterprise.


Can you please help me what can be done in this issue.


Is there any alternate Method or some Manual command or tool from which we can Upgrade them to Enterprise.


Any help would be much appreciated


29 Replies
Try to restart the computer, login with azure ad account again! MKe sure the license is set for win 10 for that user..if that won’t work please create a ticket within the admin portal! Keep me posted!!
I’ll look around some more and get back to you

No problem :)

If you end up creating a ticket please let me know what happens 

The below mentioned GPO/registry modifications are required in order to get the Windows Enterprise upgrade.

Please Disable ‘Do not connect to any Windows Update Internet locations’ GPO/Registry key.

GPO Location:

Configure the policy value for Computer Configuration -> Administrative Templates -> Windows Components -> Windows Update -> "Do not connect to any Windows Update Internet locations" to "Disabled".

Registry Key Location:

Registry Path: \SOFTWARE\Policies\Microsoft\Windows\WindowsUpdate

Value Name: DoNotConnectToWindowsUpdateInternetLocations

Value Type: REG_DWORD
Value: 0

Note: It may take upto 24 hrs. for the Enterprise upgrade to take effect.

Windows has now been enabled/activated after configuring the GPO in my test environment. =D

@adam deltinger Hi, (I know this thread is a bit old), but we are running into the same issue because our workstations live behind a Proxy Server. The networking team is not willing to allow this traffic through the firewall, is there any other way to activate behind a proxy?  MS 365 E3 ( Win 10 Ent subscription).  Test Workstations activate in DMZ...