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Office 365 issues – The Story continues

In mid-January I worked through a real fight to get my laptop’s Windows Insider Preview upgraded to build 17074 and then, to get Office 2016 (Enterprise E3 plan) installed. That fight made me write three longish posts about it. If you have 10 minutes to spare, grab a cup or glass of the beverage of your choice and read about this fight, here are those links in chronological order (oldest first):


Here’s a quick summary for those in a hurry: I needed four days and countless re-built deployment images to finally get build 17074 installed, Office activated and connected, with SharePoint and OneDrive for Business services also included. It took days but finally when everything was done, I was breathing normally again. Then, Office simply informed me that it was deactivated and refused to activate, whatever I might try to bring it back to activated status.

I finally gave up, using only the Office online browser apps until Insider build 17093  released on February 8th. Then, I built a new custom 17093 deployment image inside of Hyper-V. At this point I’d noticed that if I installed Office suite in Audit Mode when customizing my image, when that image was deployed and Office  activated using end-user O365 / Azure AD credentials, my system got “confused.” In fact, it showed two Office SKUs. In the following screenshot the Office installed in Audit Mode which naturally was not activated shows as Grace Edition (blue highlight), and the same Office with end user activation appears as a Subscription Edition (yellow highlight):

One Office installation shown as two SKUs. Click screenshot to open this image, enlarged on a new tab.

For reasons still unknown to me, this caused Office to only work over a five-day grace period. Then, it deactivated and started throwing account errors.

OK, I decided to build my custom Windows image as usual, with one exception: I did not include Office in that W10 image. I did, however, install my usual stuff such as Visual Studio, ADK, web browsers, video editing software and so forth, sysprepped and deployed, leaving Office installation for later on.

This seemed to work. Here, only one SKU is shown:

Only one SKU. Click screenshot to show enlarged in new tab.

Of course, things are never so simply as they seem. Office 2016 worked perfectly with just one exception: I couldn’t connect SharePoint and OneDrive for Business from my secondary O365 account. I tried several times a day, always getting the same error message:


On Tuesday, February 13th, just after midnight and five days after deploying the custom image to this laptop and installing / activating Office, after finishing a Teams chat with my partner Ed, I had to reboot. Skype for Business is set to auto-start, it’s always the first O365 app to tell me if there are any issues. There were issues indeed:

Once again, five days after activating Office it was deactivated and I could not re-activate it.

This story will continue when I figure out what to do. I am not sure if I should start from scratch and spend a few hours preparing a new image, or choose the faster way and re-deploy my 17093 FFU image only to get Office to partially work (without secondary O365 account resources) for five days. Deploying FFU instead of WIM only takes a fraction of the time (read more here) so I might choose it as the easy way out. Thinking about my situation I have to ask: “Is this what the future will be?” Will I have to I re-deploy every five days, after Office deactivates itself? Gosh, I sure hope not!

I am somewhat annoyed now. I’ve now spent a full month chasing Office activation and account errors. Luckily, I still have an unopened bottle of supermarket bourbon. Cheers!


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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