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I had an unlicensed (but legitimately obtained) copy of Windows 7 on a VM. I upgraded with the $40 Windows 8 upgrade, and it activated without a hitch.



Do you mean your Win 7 was on a volume license?

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Sorry, I should have said "un-activated." It was a boxed version of Windows 7 Home Premium that I had run out of valid licenses for, so I just never activated it. I was then able to use the upgrade edition of Windows 8 to install and activate successfully. I have since reverted back to my un-activated install of Windows 7.

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