Windows 10 Supscription license (M365 E3) not Activating

Copper Contributor

I upgraded my account from Office 365 Business Pro Plus to M365 Enterprise E3 licensing.  I am testing the subscription license activation for a client and things are not going to plan.  I have followed every TechNet and forum article that I could find (some MS some not) and nothing seems to be working.  I have used slmgr /upk then /cpky to remove the "Evaluation" key on to test on a clean install (re-image) and have tried with the Firmware based key, all to no avail.  So I opened a ticket with MS.  The subject line of the first ticket clearly said Windows 10, but it got routed to an O365 technician (who basically said he couldn't help and then closed said ticket). So I opened ANOTHER one.  This time, I get told that the subscription license only provides an upgrade path from Pro to Enterprise.  Well, being a bit aggravated by this point, I basically replied that I refuse to believe the company that gave us Intune and SCCM now suddenly believes that no machine will EVER need to be reimaged and that I felt that the ticket needed to be escalated.  My "escalation path" from Ms. Bhawna Punyani was to come here and ask the same question yet again.  So here I am.  How in blazes do I get this subscription to activate.  The system is AAD joined, and registered in Intune if that matters, and nothing I have tried works.  Please advise.

5 Replies

"Hi Chris_Ruggieri,

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@Chris_Ruggieri is the current Win 10 pro OS licensed and activated? I only ask because I had a similar issue when I purchased M365 E5 & saw several post similar to my issue in that in order to get the OS to activate the subscription license and migrate to enterprise you had to have a valid pro subscription for windows 10 currently activated you couldn’t just download window 10 and have it activate as enterprise when you logged in. Which was inconvenient as I was testing and had to buy a win 10 pro license"



@sxc7886I've tried it both with my client's KMS activation and without.  Neither way was successful. I've also tried using the Evaluation edition, which should have provided the same results.  My client has asked me to test this out before they buy several thousand M365 E3 licenses.  If I can't get it to work or if it is this big of a fiasco to activate every one of them, then I can assure you that they will not be subscribing.  This should not be this difficult.  


Step 1: Install Windows

Step 2: Join to Azure AD

Step 3: Assign License

Step 4: It activates


End of story. We should not have to be jumping through 4 million hoops on this and I will not buy a Pro license just so that it activates.  That's insane.  Are we going to need to install Pro every single time we reimage a machine???  That's bonkers.  This should be a simple Tier 1 fix not a (what is now going on) 3 week affair.

@Chris_Ruggieri I have this issue on M365 Business. When I connect users to Azure windows10 become Windows10 Business but Operating system is not activated 

@Chris_Ruggieri Did you get this issue resolved?  We are dealing with the same issue and have been working with MS for four weeks and they have no idea why it is not working for us.

In a nutshell? Nope. I bought a Pro license for that one machine and my client decided NOT to move on the subscription model and in fact are starting to train new arrivals on either MacBook or Linux Mint. You would think this would be an easy hop, but MS licensing was created by and can only be understood by people with a PhD in craziness. So, far the client has move 400 servers over to Linux boxes and 200+ of their 7000 endpoints over to either Mac or Linux. MS lost a major customer on that one. My contact with that company expired and they were in good shape to keep going without me so I've moved on to a different engagement.



We have experienced a difficult activation for some clients.

The environment is based on an On-prem AD with Azureadsync to AzureAD but not with writeback.

Users gets synced as well but there is no writeback there either.


What seems to have happend is that local on-prem computers failed to activate with the M365 E3 license and once synced to AzureAD, there is no way to force the client to get the license key again.


The only thing that worked for us was to delete the user profile on the computer --> reboot --> login with the UserPrincipalName.

Now the license key for Enterprise will not go away, even how hard I try to clear it and force the OEM or generic Windows 10 key on to the computer.


I saw that you do not have anything to do with the customer anymore but this might help you in the future as it was not documented anywhere what I could see.