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Watch a Machine Get Upgraded from MS-DOS to Windows 7 [Video]

What happens if you try to upgrade a machine from MS-DOS to Windows 7? One curious geek ran the experiment using VMWare and recorded the whole, surprisingly fluid, ride for our enjoyment.

Andrew Tait was curious, what would happen if you followed the entire upgrade arc for Windows from the 1980s to the present all on one machine?

Thanks to VMWare he was able to find out, following the upgrade path all the way from MS-DOS to Windows 7.

Check out the video below to see what happens:

Chain of Fools: Upgrading Through Every Version of Windows [YouTube via WinRumors]

Jason Fitzpatrick is warranty-voiding DIYer and all around geek. When he's not documenting mods and hacks he's doing his best to make sure a generation of college students graduate knowing they should put their pants on one leg at a time and go on to greatness, just like Bruce Dickinson. You can follow him on if you'd like.

  • Published 03/3/11

Comments (25)

  1. Thomas

    I think he forgot Windows ME?

  2. Aron

    EPIC! <3

  3. Khai

    @Thomas

    we all want to forget Windows ME.

  4. Jason Fitzpatrick

    @Thomas: What is this Windows ME you speak of? ;-)

  5. Rebs

    it is the devil incarnate

  6. Art

    Well done – awesome video!

  7. dave

    brings back memories…thanks!

  8. Spanky Dan

    Where was Microsoft BOB? Now THAT was epic.

    And did I miss Windows 286?

  9. Tonifero

    yes, the video is excellent and yes, is beter to forget win ME

  10. Dave

    Did anyone notice one of the user names was twatface? lol Gotta love this guy!

  11. Luie

    Window ME was left out because it could not be upgraded to 2000, it says it right in the video.

  12. Red

    Found this so interesting and fascinating that all the old installs and service packs were still around for the experiment :D

  13. Andy

    I found it hugely depressing. After watching this I vividly remember countless nights doing installs and re-installs and being away from my wife, working while she slept.. Probably why we got a divorce.

  14. HKB

    wheres the mouse in the first few minutes??
    the user was typing everything?

  15. Tathrim

    I’m assuming 64-bit wasn’t used for the operating system in Win 7, because Reversi is a 16-bit application.

    That begs the question – Should Windows 8 still have a 32-bit version? 25 years is a bloody long time to support 16-bit emulation, given that 64-bit Win 7 is more prevalent than the 32-bit OS (going on the Steam HW survey statistics).

  16. Hatryst

    Did anyone read the video description on YouTube? It includes an FAQ…

    “1) Why Didn’t you Install ME?

    Since Windows ME cannot be upgraded to 2000, I chose to install 2000 straight from 98 as it was chronologically the next release. I might do an “alternate history” version to see what going from 98 to ME to XP looks like.”

  17. Torengo

    lol, twatface

  18. Chook

    - forget ME it said in the video ME was not used because of upgrade limitations.

    Cool video, a blast from the past and still going strong.

  19. ITMan

    Good video, have done most of the above in my time (excluding winows 1/2), but got a couple of questions regarding the upgrade path. What size RAM and hard disk was used for the VM to go from DOS to W7? Was the VM adjusted along the way to allow for the greater software requirements

  20. derekr54

    Very interesting little video,well done and Twatface cracked me up!

  21. Yazeed

    Can anyone please tell what is the difference between installing windows using the well-known way or this one? because I do not see any difference between them. Thank you.

  22. superfahd

    I remember once a long time ago when I was using Windows 97. I did something horribly wrong and had to reinstall windows. I dont remember all the details but I think I had a Windows 95 to 97 upgrade pack instead of the entire thing so I couldn’t install it directly.

    In the end my install/upgrade went like this: Dos 7 -> Windows 3.11 -> Windows 95 -> Windows 97 upgrade!

  23. Yullrich

    Is it just me or does it feel that people do not appreciate the value of computers any more…it seems just like any other toy? thank you for the trip down memory lane(… sigh…)

  24. Anthrogeek

    Great video, well done!! However, twatface as the user caught me by surprise.. but it was hilarious. :)

  25. arahman87

    @HKB

    The first few OSes were Command-Line, and made little to no use of the mouse.

    @Tathrim

    I would hazard a guess that Windows 8 would include a built-in VM for the 16-bit apps. Consumer Virtualization has matured greatly, and it is the best way to provide backwards compatibility for older programs.

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