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.
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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.