Chain of fools : Upgrading through every version of Windows

Here is a video presentation covering an experiment I recently performed, in which I upgraded through every major version of Windows. Below that I'll try and add some detail that I didn't cover in the video.

My parents have had a PC since I was about 5, so I have many nostalgic memories about early versions of MS-DOS and Windows. This is probably why I chose this project, as it gave me a chance to relive some of those memories, and finally gave me something to do with my cupboard full of old computer software.

I got the idea from a 90s computer magazine article I vaguely remember (possibly from PC Format?), which essentially did the same procedure but only from Windows 3.0 to Windows 98. Since virtual machine technology is much more mature now, and there are four additional versions of windows, I thought it would be a great time to repeat the experiment. I installed Doom 2 and Monkey Island as tester applications, as I found the installation disks for them while I was looking for Windows disks, and those were two of my favourite games from the period (and still are).

The whole procedure took 3 days, of which approximately 12 hours was spent doing the actual installing - the rest of the time was spent trying to obtain valid copies of windows. One of the biggest problems was that Windows 95 and 98 came in two versions - Upgrade and Full. I had old disk copies of every Full version of Windows, but they cannot upgrade earlier versions. Luckily I was able to borrow a Windows 95 upgrade disk from a friend, and 98 was installed by renaming system files to trick it into upgrading.

Another hurdle that had to be overcome was one of system requirements. MS-DOS uses the FAT16 filesystem, which only supports partitions up to 2GB in size. This was no problem until Windows XP, which required a comparatively large amount of space - at this point, the filesystem was converted to FAT32 and resized to 25GB using the GParted Linux LiveCD, which is a fantastic little utility. For Windows Vista, the partition had to be converted to NTFS using the built-in converter tool.

I was pleasantly surprised to see the DOS versions of Doom 2 and Monkey Island still running in Windows 7 after all these years. Microsoft has had a lot of stick through the years (not least from me) but this really is a laudable achievement.

If I were to perform the experiment again, I would probably try finding a few Windows 1.0/2.0 applications and installing them to see if they were picked up in 3.0's program manager. I was unable to find
any native Windows applications that ran on 1.0/2.0, but I'm told early versions of Word and Excel did.

There is also an alternative upgrade path - instead of going from 98SE to 2000 to XP, it is possible to go from 98 to ME to XP. The former route was chosen as Windows 2000 was chronologically the next release after 98, and in any case I didn't have a Windows ME CD having never owned it. Maybe I'll release an "alternative history" version of the video that does just that, as I still have a VMWare snapshot of the 98SE installation before 2000 was installed.

FAQ

Why Didn't you Install Windows 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.


Did Doom 2 and Monkey Island work in Windows 7?

Yes. Sorry I didn't point that out explicitly in the video.


Can you do the same thing with Mac OS?

I don't know enough about Mac OS to be able to say, and I would not be the best person to do that experiment as I have never been a Mac user.


Where are you from?

Scotland.


What's that beeping noise in the background?

My smoke detector - its battery is flat :)

Thanks for watching.