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steveskingle
Contributor
Contributor

Windows Server In Place Upgrade Issue - Setup Couldn't Start Properly

Good Morning

Ok, on the face of it this looks like a windows issue. I don't believe it is so bare with me!

I have a VSphere infrastructure of approx. 80 servers. 10x on 2012 R2, 50x on Windows Server 2019 and 20x on Server 2022.

Before anyone says it, I don't always in-place upgrade and would much rather rebuild a new server when it comes to upgrading, but sometimes that isn't possible. I in-place upgraded a few machines to server 2022 about 8 weeks ago, all succeeded.

I tried doing an in-place upgrade a few days ago and instantly I was hit with the "Setup Couldn't start properly. Please reboot your PC and try running windows 10 setup again".

I have done everything I can:

Disk Cleanup incl system files, All updates done, tried as local admin/domain admin, Disable/uninstall anti-virus, Disable startup files, dism restore health, sfc, Isolate server from network. Honestly, i've tried it all.

Then I thought i'd check a few other servers. Every single one of my servers gives me the same error. If I create a new server and domain join it, it works, but on all of my existing servers it doesn't, even if I mirror hardware settings from old servers, it still works on new ones. 

I'm at a total loss. The fact all my servers are doing this to me tell me it might indicate something with Vmware rather than Windows. 

Has anyone got any ideas at all???

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steveskingle
Contributor
Contributor

FYI Ended up being a windows/domain issue. If I take servers off the domain it works fine, so not a vmware issue at all......

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