Could not Upgrade Windows 10 from Pro to Enterprise using Microsoft 365 E3

[Prakash Thakor]

Our Setup:

• Dell Desktops with Windows 10 Pro 1803 Activated and local AD joined.

• Local domain synced with Azure AD \ Office 365.

• Users have Microsoft 365 E3 licenses.

We have Microsoft 365 E3 licenses, which include Windows 10 Enterprise. I have tried to upgrade from Windows 10 Pro to Enterprise edition using these steps but still they are not upgraded to Enterprise .

https://aadguide.azurewebsites.net/aadjoin/ https://docs.microsoft.com/en-us/windows/deployment/deploy-enterprise-licenses

Some Troubleshooting :

1. dsregcmd /status shows AzureAdJoined status is YES; also this desktop is showing in Azure AD Portal.

2. Could not find any Task Scheduler https://docs.microsoft.com/en-us/windows/client-management/mdm/enroll-a-windows-10-device-automatica...

Tried troubleshooting steps as per following URLs, but still could not find any clue:

https://social.technet.microsoft.com/Forums/windows/en-US/78afe9a3-3449-4efb-bf20-e3ad5f2b32a2/windo...

Any help would be much appreciated.

Please see the attachment for your reference.

Thanks,

[#2]

How the machine license is activated, OEM or VLSC key?

[#3]

You need to have a valid PRO license
Set the Windows 10 license for users i portal?
Logged into Windows with azure account?
There’s also a gpo setting that must be set most often! Can’t remember it now but i’ll Check

Adam

[#4]

Are you still facing the issue?

[#5]

@Prakash Thakor 

Hi,

Having a Dell 9370 I've been fighting the CSP E3/E5 (tried both) activation for a while. I don't need enterprise but wanted to try so used a trial and then bought an E3 to try and make it activate.

Same issues as you stated, joined to the AzureAD (VERY painful as joining AzureAD was not provided as an option using the local admin Microsoft account I originally set machine up with).

First step was jumping through hoops …. created a brand new Microsoft account, added it to the machine as another local admin account. Removed myself from my companies Office accounts, and finally the 'add to AzureAD' showed up as an option.

Great, except like you the machine would not activate. I waited hoping it was just a timing issue, nothing. Opened a call, spend 5+ hours over two days with Microsoft support. Everything looked right and they couldn't figure it out.

Finally, I was reading one of the many articles on the challenges with E3 activation, this happened to be on the Hybrid AD scenario (we are 100% cloud so not the issue I have however I was reading everything). In the article, it was stated that MFA can cause activation to NOT work. As a Tier 1 CSP we are required to have MFA enabled (and we do so as a best practice both internally and we recommend to all our customers). 

I turned off MFA, logged off and back on, BINGO, the machine was magically Windows 10 Enterprise.

Hope this is helpful