Dude Upgrades DOS 5.0 Setup Through Every Major Version of Windows

Paul Lilly

Do you remember mucking around with Autoexec.bat, Win.ini, and floppy drives, or typing Win from the Windows directory to load Microsoft Windows? Our apologies if you've tucked these memories away in a place you thought they'd never be resurrected, but if you want feel all nostalgic reminiscing on your long journey from DOS to Windows 7, you have to check out this nearly 10 minute YouTube video.

Poser "TheRasteri" attempts to follow an upgrade path through every major version of Windows. To do this, he set up a virtual machine with MS-DOS 5.0 using VMware. The video begins with the narrator explaining that "this is an experiment to test the upgrade facility of Microsoft Windows operating systems" in hopes of "shedding light on how the Windows upgrade process has changed over the years."

Surprsingly enough, the entire upgrade path goes mostly without a hitch, and by the time he got to Windows 7, some legacy applications remained, like Card File, Recorder, Terminal, and Reversi, among others. Pretty impressive that, should you want to, you can upgrade through nearly two decades of Windows OSes.

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