I doubt very many of you ever used Windows 1.0 (I certainly didn’t: 3.0 was the first time I used Windows). Charles Arthur writes about an interesting experiment conducted by Andrew Tait to test how well your system would work if you somehow needed to upgrade through all the major Windows versions:
The question is: how robust is it? Can you really do all that updating? You have to start with MS-DOS 5.0, of course, because early versions of Windows needed that.
It’s a bit hairy and config.sys-y in the early versions up to 3.1.
But what’s really impressive is that Doom 2 and Monkey Island — installed right at the beginning — work all the way through, right up to Windows 7. Well, apart from in Windows 2000, where it hung at the start (lack of DOS support).
Well done Andrew Tait, alias Rasteri, the YouTube/Reddit user who had the enormous patience to do all this. Especially for sounding like Sean Connery all the way through. “It is indeed possible to upgrade through every version of Windows… and have some settings remain. This is nearly 20 years of application compatibility and Microsoft should be applauded.”
Of course, the real stumbling block to doing this would be the hardware: nothing that was available in the Windows 1.0 era would be able to run the far more demanding software of the Windows NT family of operating systems. To get around that, Tait used VMWare’s virtualization software:
