You Can Upgrade MS-DOS 6.22 To Windows 8, If You Really Want To [Stuff to Watch]

Tim Brookes 09-09-2014

There are some videos on the Internet so crazy that you just have to see them to believe them. Things like prisoners performing “Thriller”, Chocolate Rain and this – a single MS-DOS installation being upgraded to Windows 8 in one sitting.


YouTube user Voltage^ condensed twenty six years of desktop computing into a short burst of nostalgia, with some notable highlights. And luckily, you don’t need a full hour to watch the whole thing – there’s a condensed version.

Why? How?

Let’s not pretend this is useful, because it’s not. If you want to run Windows 8, you should simply install Windows 8; in fact this isn’t even possible on real hardware. Not like that game of Civilization that went on for ten years Game Over Isn't An Option: These Games Never End Earlier this month a tale emerged of a Reddit user who had been playing the same Civilization II game for a total of 10 years. While many massively multiplayer games could take a lifetime to... Read More .

The video was created with the use of virtualization software VMware 8, which can be configured to meet the requirements of pretty much any operating system you throw at it. For context, Windows 1.01 required 192 KB (0.192 MB) of RAM in 1985, Whereas Windows 8 requires at least 1 GB (1000 MB Memory Sizes Explained: Gigabytes, Terabytes, and Petabytes in Context How big is a gigabyte? What is a terabyte? Will you ever need a petabyte? Let's explore computer storage sizes in perspective. Read More ) in 2014.

An IBM compatible like the Tandy 1000 would set you back $1,200 in 1984, which is roughly $2,600 in today’s money. You can get up and running with Windows 8 for much less than that How To Buy A Laptop On A Budget But how do you choose the right laptop, and what can you expect from its performance? Read More  today, and save even more if Google has anything to say about it Everything You Need To Know About Switching To A Chromebook Chromebooks run a slimmed-down operating system optimized for getting on the web with just the Chrome browser and Chrome apps. Can you switch to a Chromebook? Read More .

Windows 8 killed off support for many remaining DOS processes, so by the time Windows 8 is installed very few still work. There is still an MS-DOS folder left over, and programs written for Windows 2 and 3 are still operational and at the very end of it all the volume label remained “MS-DOS_6″ as it was originally set. Impressive or pointless, you decide.

Let’s Start

You probably don’t have too much interest in dedicating one hour and seven minutes of your life to watching the entire procedure in realtime, but just in case you do here’s the whole thing. Stick it on while you’re doing something and be transported back to an era of driver disks and unfilled warranty cards.


It’s far more likely that you’ll want to watch this shortened four minute version instead. Everything whooshes by in a blur of command lines and progress bars, but you’ll see enough ochre colour schemes and utilitarian UI elements to get your fix.

A Wolfenstein 3D save created with MS-DOS 6.22 is used as a test throughout, with the same desktop shortcut persisting from Windows 95 all the way through to Windows 8. Here are the exact steps performed by Voltage^ to create the video, taken from the YouTube description:

1. Install MS-DOS 6.22
2. Install Wolfenstein 3D as a test
3. Install Windows 1.01
3. Upgrade to Windows 2.03
4. Upgrade to Windows 3.0
5. Upgrade to Windows 3.11
6. Upgrade to Windows 95 (Used Upgrade Version)
7. Upgrade to Windows 98 (Used Upgrade Version)
8. Converted file system to FAT32
9. Upgrade to Windows ME (Used Upgrade Version) 
(could have replace this with 2000, but choosed ME for faster install! ME and 2000 won’t work!)
10. Resized Partition with Linux Live System to 40GB
11. Upgrade to Windows XP
12. Converted the file system to NTFS
13. Upgrade to Windows Vista
14. Upgrade to Windows 7
15. Upgrade to Windows 8

Of particular interest is step 10 where the file system is manually resized with a Linux, which just goes to show you can never underestimate the usefulness of a live Linux distribution Windows Users: Here Is Why You Need A Linux Live CD Read More  like Hiren’s Boot CD.

Fancy A Go?

Voltage^ has provided links to downloadable disk images up to Windows ME (including blacklisted serial numbers!) in the original upload description so you can replicate this process if you really want to. While that’s unlikely, you can always download an old favourite, fire up VirtualBox How to Use VirtualBox: User's Guide With VirtualBox you can easily install and test multiple operating systems. We'll show you how to set up Windows 10 and Ubuntu Linux as a virtual machine. Read More  and rediscover an environment you were once confined to from a different perspective.


Did you get nostalgic watching those progress bars fill up, or did I just make you feel old?

Affiliate Disclosure: By buying the products we recommend, you help keep the site alive. Read more.

Whatsapp Pinterest

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. ja
    January 12, 2016 at 1:38 pm

    lol. 1024 not 1000. Who wrote that? That's basic knowledge.

  2. likefunbutnot
    September 9, 2014 at 7:59 pm

    You certainly can go from DOS6 to Windows 8 on real hardware. I don't THINK it can get to 8.1 without an upgrade, but late-gen Netburst (Pentium 4) CPUs will work in Windows 98, PCI-e graphics cards, SATA hard drives and all.

    I'm not completely sure I could say the same thing about anything new enough to run a Core2 Duo or Athlon X2, but it's really more an exercise in patience and careful hardware selection than anything else.

  3. John Williams
    September 9, 2014 at 5:40 pm

    Fantastic how much incredible progress has been made in less than a lifetime.

    What still amuses me now is that I had a full-on "Windows" style program running on DOS, called "Framework" by Ashton Tate. Everything was already there except the fancy graphics - A full powerful word processor, database and spreadsheet - even rudimentary graphics once we got through VGA, XVGA, E-VGA etcetera!
    And it all worked on about 64Mb of RAM with a CPU running at 300MHz. Not a Giga-anything in sight. No HDD, just 2 floppy discs.

    Still it was all a step up from playing chess with the Open University's mainframe using a Teletype machine. Eeee, when I were a lad, there were no mouse, no VDU screen and we all a t'wear lab coats to go near the printer. It were vicious and would have your hand off in a blink.

  4. J.Bink
    September 9, 2014 at 12:53 pm

    To answer the question at the end of the article: nostalgic. Totally nostalgic.

    It's pretty amazing to think that you can actually upgrade from Win. 1 to 8 like that. I wonder if something like that is possible on other platforms, like Mac or Linux?

    • Tim B
      September 9, 2014 at 11:45 pm

      I looked, and I couldn't really find anything for any other systems. Nothing else has quite the continuity that Windows has enjoyed over the same period – Microsoft essentially made lots of incremental updates.

      Glad you enjoyed the trip down memory lane :)

  5. Guy Fuller
    September 9, 2014 at 3:05 am

    This article is worthless.