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June 2, 2020

W10 Insider Skip Ahead & O365 – Redmond, we have a problem

As I have revealed in several “War Stories” posts here at Win10.Guru, I’ve had major issues with Office 365 running on Windows 10 Insider Preview Skip Ahead builds. On two occasions since January 2018 I’ve thought that I finally had these issues resolved (read more). Alas, both solutions seem to have been pure coincidence. Even now, those issues remain. After each Win10 upgrade, O365 loses its activation which makes all Office applications unusable. The only workable solution I’ve found is to perform a clean install for each new Skip Ahead build, and remove all previous installations from my O365 account > Detected installs, and start over from scratch.

O365 is extremely important to me. I have no use for a Windows 10 computer with non-functional, unactivated Office suite. I depend on using Outlook to send, receive, reply and forward my emails. I fully depend on Word, Excel and Access to edit, save and share my documents. I am fully dependent on my ability to open, edit and collaborate with Office files on OneDrive, OneDrive for Business and SharePoint. I might not say “Office is my life,” but I would most definitely say “Office is my living.”


I always install O365 using Click-to-Run installer from my primary workplace / Azure AD account. I then add additional “connected services”: my secondary workplace / Azure AD account and two personal OneDrive accounts. All in all, I have two workplace accounts and two personal OneDrive / Microsoft accounts always connected to O365.

At this moment, of the last seven Insider Preview Skip Ahead build upgrades released, I have lost O365 activation in six of them. Because uninstalling / reinstalling O365 does not work, my only option has been a fresh clean install of the OS on average twice a month. With the usual software I need and must have, including in addition to O365 stuff like Visual Studio Enterprise (almost 30 GB ) and Windows ADK (over 7 GB ), I have been forced to perform a clean install twice a month that takes over 6 hours (Windows + all required software) to complete. Fundamentally, I have nothing against this. I am a tester and love testing different scenarios and would be doing regular fresh installs anyway. It’s just that I am starting to get a bit annoyed. Each time the Insider team releases a new Skip Ahead build, I already know it means a sleepless night (I’m in Europe, so new builds usually appear late evening, my time).

Not exaggerating at all, I can confidently say I have spent more than 100 hours to study, inspect and try to find the reason for this issue. In my opinion, it is not acceptable that O365 loses license activation whenever Windows 10 is upgraded. I admit that remaining on Skip Ahead builds is my own choice, though. I might not have these issues if I switched to the latest official release. However, I have selected to test Skip Ahead builds for a reason: I want to make my mark, to participate in testing future builds to be able to help and assist my fellow Windows 10 users better. I write tutorials on TenForums.com; I make Windows 10 videos for my YouTube channel; I cover Windows 10 in depth and at length right here for Win10.Guru. Thus, I want a seat in the front row, so I can see where Windows is going. I also want to be prepared for questions from admins and power users who might have issues with Windows 10.

What Might Cause This?

I have a few theories. The one I think is closest to the real cause about which I wish I could impart a meaningful clue to both the O365 and Windows Insider teams is this: In my case, all four accounts connected to O365 have valid Office licenses but naturally only one of them is used to activate Office. Both workplace accounts have a license through my O365 Enterprise E3 subscriptions, and both personal connected OneDrive / MS accounts obtain a license through O365 Home subscriptions.

I think that after the upgrade, Windows 10 and especially O365 gets confused because of multiple accounts connected to it, each with its own valid O365 license. To make things more confusing, the pool of connected accounts includes two different types of licenses — namely, Enterprise E3 and personal / home. This is what happens when I upgrade, as shown in a screenshot from a tweet I posted a few builds back:


My theory is supported by what actually happens when I upgrade to the next Skip Ahead build. O365 forgets my Enterprise E3 activation and asks me to sign in with my primary MS account, my Windows 10 sign-in account. In other words Office simply defaults to my personal MS account after the upgrade when not being able to check the Enterprise license status. It appears that it completely “forgets” the Enterprise workplace accounts. Instead, it asks me to sign in to activate O365. After accepting the default MS account login, Office tries to activate, then reports it is unable to validate my Office license. So I say “OK, I’ll try again, this time with a workplace account.”

However, when I try to sign in with either of my workplace / Azure AD accounts, Office tells me it is unable to check the license. Instead it always presents me with the same error message:

What I do not understand is, why should the O365 product key need to be installed? Office was already activated before Windows Insider build upgrade, why is the activation removed only because I upgraded Windows?

This means that Office is completely non-functional. As most of you know, Office Repair has never really worked well (or at all). But just to be sure, I always try it when this error shows up. But really, truly, Office repair does not work in general, and it does not work to fix this specific issue, either.

What are my options? Uninstalling and reinstalling does not work. I can only do the one thing that for sure resolves the issue: a fresh, clean install, that consumes a full working day.

To add insult to this injury, I must say I am really disappointed in the response I’ve received from the O365 and Windows Insider teams to my reports of these circumstances. It seems that they share this common policy “We don’t know why this happens, so let’s just ignore this user“. All I get is questions such as “Have you reported this using Feedback Hub?” Here’s a recent exchange that shows some back-and-forth (and other issues that follow in its wake):

Not a single time have I got any direct response except “Have you reported it?” or other unnecessary questions. Doesn’t matter if I use the Feedback Hub or social media. The sole exception is @JenMsft. The thing is, Jen does not belong to the Insider team though she works with them closely. She, at least, has tried to assist me. Thanks Jen for that!

Consider the O365 team. In a direct Twitter message some time ago, they asked me to give them full details about my O365 tenant, the domains it’s using and my accounts, to be forwarded to the Office support for a thorough inspection and analysis. I gave them all possible information. But then, as seems to be their way when they have absolutely no clue as to why something is happening, I heard nothing further from them. I got no response, no more messages, no replies. I have had no help nor support from them, except some “We are sorry” and “Are you still getting these issues?” messages. No support in the real sense of that word.

What I have been hoping for is at least one clear response like Do this, then that, restart, check if Office is activated. But, really, all replies have been just questions about if I have reported the issue using Feedback Hub, contacted support, or if I have used Activation Troubleshooter, and so on. Not a single piece of usable advice.

I have been a Windows Insider since day one. I also joined the Windows Insider for Business program on day one. I am still a Microsoft fanboy in general, and a Windows 10 and O365 fanboy in particular. I love being a Windows Insider, I love to test Windows 10 and take it to its limits. I love being in a position where I can assist my fellow geeks. My experience and these O365 activation issues in no way change those feelings. I am just somewhat frustrated for not getting help. I for sure hope somebody is listening, and that help might just be forthcoming soon.

Whatever happens, I remain a keen and dedicated Windows and Office Insider,


Author: Kari Finn

A former Windows Insider MVP, Kari started in computing in the mid 80’s writing code for VAX / VMS systems. Since then, he’s worked in a variety of IT positions. He specializes in Windows image capture, customization, repair and deployment as well as Hyper-V virtualization. Kari is a proud Team Member at number #1 Windows site TenForums.com.

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