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Offline upgrade from Windows 11 21H2 without reinstalling programs


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Hi there guys,

long story short, I have some machines running Windows 11 21H2 Professional x64 in an internal, secure, network that will never ever see the light of internet and, as such, there will never be a connection to Windows Update.

Those machines are serving one and only one purpose: they drive the flexicarts of an old tape archive.

I've got a notification from the security guys asking me to upgrade, so I downloaded the Windows 11 22H2 x64 ISO from the official Microsoft website, connected it to the machine, opened the ISO from within Windows and run the Setup.exe that was in there.

There were three options, the first one, which was to update while keeping programs and personal files, was grayed out, and only the other two "keep personal files" or "nothing" were available.

This is a bit of a problem 'cause if I only keep personal files, it means that I'll have to reinstall all the drivers, the programs etc which can be a tedious task.

Ironically, I had 4 other machines running Windows 10 20H2 Professional x64 which I was able to upgrade in the same way with a Windows 10 22H2 x64 ISO by running the Setup.exe while preserving all the programs and files.

Why is the option grayed out when I try to do the same with Win11 and a Win11 ISO? What am I doing wrong?

Edited by FranceBB
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To be absolutely fair, now that I think about it, it might be that someone installed it as English UK rather than English US by mistake. I'll check on Monday to see which one it is and I'll try again.

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