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Office 365 activation help needed

Hello Everyone,

We are in a desperate need of help with our Office 365 activation/sign in issue. We have been using O365 for some time now with on prem Exchange and no cloud content on Windows 10 20H2. We have AD Connector that provides single sign on for licensing and accounts synchronization with AD.

Recently our image went haywire and it won't take updates and has other issues so we have decided to make a new one. On the new image, we have installed exactly the same version of OS, horizon agents (7.13.2) and AppVolumes just like on previous image. THe only difference this time was that we didn't optimize it with OSOT. After publishing to the pool, when new user signs in they get activated and all office products work great, but if they click sign out they will never be able to sign back in, it just prompts for email/upn and does nothing.  If a new user signs in and the writable profile is created but don't open any office application on first session then on next one they are immediately prompted to sign in to office, once they provide email/upn they get signed in but all office products show as Unlicensed Product.

For existing users with writable created on AppVolumes they are working fine and can sign out and sign back in on the old image pool but once they sign in to the new pool with new image they are immediately broken and being asked to sign in each time they open any office product.   

In meantime we also had to upgrade AV agent to 2203 due to the Start Menu error and that fixed the problem as outlined in Release notes. I was hoping this will help with activation but to no avail. It's just very strange that it's the same OS version, agents, GPOs etc and yet seeing completely new stuff happening.

Did anybody encounter a similar issue? At this point I'm not even sure what is there to blame, Microsoft, VMWare or new image? For the record we have already created another image to rule that out and getting the same result. 


Went through every single post on forum to see if there is a similar issue and couldn't find a solution. We did enable SharedComputerLicensing feature as per VMware recommendation. 

Any help would be greatly appreciated. Thank you in advance


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