Upgrades: A Journey Through Time

Be glad I’m not in charge of naming a feature film. This post will deviate a little from my usual style, in that it will be more pictures than words. Regardless, it should be an interesting trip through history.

Anyway, I’ve attempted (and succeeded) in taking a Windows 1.0 VM, and upgrading it through to Windows 8.1, in the sequence of: 1.0, 2.0, 2.1, 3.0, 3.1, 95, 98, 98SE, Me, XP, Vista, 7, 8, 8.1. I figured the ride was interesting enough that maybe I should do it again, and document it here. I’ll try to give enough detail as to what I did so any given reader can reproduce this. For starters, I’m using VMWare Workstation 10 with this configuration:

The next step is to install MS-DOS 5.

The journey begins.

MS-DOS 5, installed. Wow, that went quickly.

Now it’s time to actually install Windows 1.0. After swapping through six floppy images, I have this:

Sadly, this garbled mess is all I can get.

I can enter an app, and sort of see it, but it’s too blurry for me to figure out how to exit it. Alt + F4 doesn’t work. At least I’m not old enough to remember this. It seems painful.

Now it’s time to install Windows 2.0. At least this one’s usable. Mouse and all. I mean, I’m glad I never had to use this on a daily basis or anything, but wow, I’m shocked I could get it working perfectly. Sort of, at least. I tried opening abc.txt, and it crashed.

MS-DOS Executive. Erm… thought I was looking for Windows.

We’ll revisit Windows 2.x again later. Much later.

Now to install Windows 2.1. You’ll have to install it from DOS; otherwise you’ll get an error about not having enough memory. I don’t know why. I gave it 16MB at this point, which was more than any computer had at that time, as far as I know.

Back on the theme of apparently not having enough memory despite having plenty, when I try to run it, I get this.

I followed this MS guide¬†(which I’m impressed is even still up) to fix another error, just leading to this one. Onward, I suppose. Windows 3.0!

Heh, I get it. Windows.

Trippy. Also, nice game selection…

Now for the Windows 3.1 upgrade. Ah, 3.1, the first OS I ever used. I don’t really remember it that well though.

It manages to remember this throughout all future upgrades. Impressive!

Seems more… colorful?

It seems things are getting modern enough to go fairly seamlessly now. Or not. Windows 95 comes on a CD, complicating things, as 3.1 doesn’t recognize my CD drive. Guess things aren’t getting modern enough after all. At least I’m done flipping floppies. You can always just boot from floppy, then install from there. It’ll do an upgrade install anyway. Do remember to change the VM type to Windows 95 at this point.

It preserved that crappy background I selected, and the Ms-dos_5 disk label I’ve had for quite some time now.

It also has working sound now, and it sounds awful.

You’d probably do well to put in some more RAM now as well.

Next up: Windows 98. I put in the installer. It makes some obnoxious and loud noise. At least from here on out my CD drive works and I can do all my upgrades from within Windows.

Doesn’t my blog look wonderful in IE4?

Also, I finally installed VMWare Tools at this point (although uninstalling them to install the correct ones for XP becomes quite a point of contention – you have to use the MS uninstall troubleshooter, or alternatively as I figured out the second time around, just uninstall VMWare Tools before the XP upgrade), so things will look a bit better and be a lot less laggy for me.

Now for 98SE.

I can convert this to FAT32 now. I probably should.

Done. Also notice the user info and crappy background from 3.0 are still there (as well as the volume name).

Now to upgrade to the infamous Windows Me, after which I can finally bid good riddance to the Windows 9x line. I don’t know why it was so maligned. It installed without a hitch.

User info, check. Awful background, check.

At this point, there are important things to consider. Namely, do recall that this is sitting on a 1.5GB partition. That won’t be big enough for the XP upgrade. So I used the GParted Live CD to resize it. I’ve got no idea how big of a partition Me can handle, so I’ll resize it to 64GB. Should last me awhile. Also, it would probably be a good idea to bump up the RAM again. Seems as though it can handle 512MB well enough (also the GParted Live CD won’t seem to boot on only 64MB anyway). Finally, I uninstalled VMWare Tools. In my practice run, I didn’t, and had to jump through hoops to get it upgraded once I got to XP.

XP, the OS that won’t die, and IE6, the browser that won’t die.

Despite being a lot more “modern” than its predecessor, XP is still ancient by modern standards, and people would do well to realize that sooner or later. Unfortunately, my workplace actually still uses this. Fortunately, I don’t touch those computers unless something’s wrong with them. My blog looks just about as horrible in IE6 as it does in IE4. Also, I bumped the VM up to 4GB of RAM (it only sees 3 though). I also have to convert the disk again, to NTFS, in order to install Vista.

Hmm… it lost the crappy cubes background. Kept the computer and workgroup names I assigned it back in 3.x though.

For some reason, my VM also kept the “View Channels” Quick Launch icon.

Windows 7.

At this point, not much remains unchanged. The wallpaper’s changed itself yet again, and even the taskbar icons that were there since the 98 install are gone. Kind of disappointing. Well, this will be rather boring from this point forward, but you’ve made it this far. Onward, I suppose.

Windows 8. Nothing to see here.

At this point, it looks fairly obviously “stock,” with the exception of the compatibility report on the desktop. A few things stay until the bitter end, but they’re not very obvious. I’ll cover them in a bit.


Yep. Still looks fairly stock. This stopped being interesting awhile ago.

This step marks the last of this journey. Beginning with Windows 1.0 and ending with 8.1, this is the result. I expected something a little more interesting in the end, especially since quite a bit of stuff from early on kept itself throughout the XP and Vista upgrades.

To recap, things that didn’t make it:

Desktop wallpaper

Quick launch icons

Most applications

Things that did:


Yep. That’s MS-DOS 5 alright!

The volume name.

What is this, I don’t even…

A bunch of old Windows and DOS files. Strangely enough, I can even get some Windows 2.1 apps to run all the way through 8.1. I don’t actually know what this one does though.

The Windows 2.11 Control Panel. Now that’s a bit more interesting.

I wonder if it actually does anything. Now that I’m done with my experiment, it shouldn’t matter if I trash this VM…

Strangely enough, yes.

The only setting that works is the one to switch mouse buttons. But it works nonetheless. Finding that out kind of made this whole thing worth it. Although I suppose it doesn’t go with my topic of things preserved through OS upgrades, since you could probably just copy in that CONTROL.EXE and try it. I doubt any of this information is useful, as no computer that ran Windows 1.0 in the real world could¬†ever be upgraded to anything even approaching a modern OS, but it is possible in a simulated environment, with the results described. You’ll probably never actually need to do this, but… it’s fun to do when you’re bored.

One Response to “Upgrades: A Journey Through Time”

  1. Anonymous 1

    This was really interesting! Though I’m sure if you used real hardware or didn’t install VMWare Tools it wouldn’t have been so smooth & you would have faced endless errors & problems along the way.

    Oh & why didn’t you include Windows 2000? It was technically released before Millennium even though in the same year but it was actually the first pure 32-bit OS before XP! It wasn’t as popular though because it was targeted mainly at businesses & was only released in Professional & Server Editions IIRC… Nonetheless I think it would have been a nice addition & may have eased up the transition between ME & XP.

    And by the way, if you still have the VM please don’t delete it, Windows 10 should get released this year & it would be great to see the upgrade continue!

    Amazing post, cheers!

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