How To Install MS-DOS 6.22 And Windows 3.11 In A Virtual Machine

Sitting in front of our modern PCs, it’s hard to imagine a time when things weren’t as smooth, easy and inutile as they are today. In my recent review of Parallels Desktop 14, I mentioned that I set up a virtual machine to run MS-DOS 6.22 and Windows 3.11. Here’s how I did it.

I decided on the combination of DOS 6.22 and Windows 3.11 as that was the last mainstream generation of software that relied on a command line operating system. And I figured that it would pose the most challenges to install.

As I’d recently installed Parallels Desktop 14, I decided to use that for my DOS/Windows machine.
I should note that although I downloaded disk images for DOS and Windows, I still have my original floppy disk installation media so I didn’t feel too bad about downloading software that was released in 1993 and has long-since been out of mainstream use.

I sourced my copies of the media from The Legacy PC Project. If you still have the original media and a floppy disk drive (I have an old USB one for just this sort of occasion) then you can create your own disk images if you have some spare time.

Also, this procedure should work with the free virtualisation software, VirtualBox as well as Vmware Fusion.

Creating the Virtual Machine

It turns out that installing DOS and Windows is actually the easy bit once you have the media. The real challenge was in creating a VM that would boot up at all – at least that was my challenge.

I started by visiting AllBootDisks and grabbing a DOS 6.22 bootable ISO. AllBootDisks has bootable images for a bunch of older operating systems. I grabbed a Windows 95b one while I was there as I knew one old OS was never going to be enough.

I used Parallels Desktop’s Installation Assistant to create a blank VM for DOS 6.22. There’s a Windows 3.11 option as well but figured the settings would be pretty similar. I gave it 2GB of disk space – which is about 20 times more than my first PC had (120MB and it was beast of a system in its day with it’s huge 4MB of memory and 486 processor).

Getting minimal DOS running

I then attached the DOS 6.22 boot disk I previously downloaded as a CD/DVD – this is important – and followed some instructions I tracked down at Parallels’ support forums.

This instruction described how to partition the VM’s hard drive, format it so it’s bootable and add a few files so that I ended up with a bootable hard drive.

By the way, it’s really important to change the boot order of the virtual machine so that it prioritises the floppy drive and CD/DVD over the hard disk.
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Once that process was complete, I had a working installation of MS DOS

But what about all of DOS?

If you want a full installation of DOS, with all the extras like DOSSHELL, SCANDISK and everything else, connect Disk 1 from the set of images downloaded from The Legacy PC Project, boot from that and follow the installation instructions for MS DOS.

Once the installer is done with Disk 1, you’ll need to connect each disk in order. But the whole process is way faster than using installation floppies on an old computer.

Installing Windows 3.11

Once DOS is up and running, installing Windows 3.11 is a walk in the park.

Connect the image for the first Windows 95 installation media, switch to the floppy drive by typing a: at the command prompt and then type setup.

Swap the connected disk images as you’re prompted and within a few minutes, you’ll have a working Windows 3.11 installation.

By the way, don’t forget that you’ll need to type win at the command prompt to launch Windows 3.11. Or you can simply add the word win to end of the autoexec.bat file (a text file that provides instructions when a computer running DOS starts up) so it’s starts automatically.

Once you’ve done that, you can use what you’ve learned to install all sorts of other old operating systems. I’ve got Windows 95 running as well and I’m going to get OS/2 – IBM’s short-lived but pretty cool Windows competitor – up and running as well.