I learned to program back on an old TRS-80 Model III computer as a kid. Long before Windows and even DOS, most home computers required you type in programs or load them from cassette tapes. If you were really rich, you might afford a floppy drive, but that was an expensive luxury I never had. My next computer was an IBM XT, and it ran the advanced and stalwart DOS 3.30 – which was dramatically better.

Running those old operating systems today requires you either buy one of those old systems and keep it running, or you have to emulate them. You can easily emulate DOS 3.3 and Windows 3.0 and higher on VMWare or Virtualbox, but going earlier than doesn’t seem to be supported anymore.

Enter 86Box – an emulator that lets you emulate REALLY old machines. In fact, I was able to get Dos 3.2 running Windows 1.0.

Here’s what you’ll need:

Part 1 – 86Box Setup

1. Download 86Box and install it (source is on github).
2. Download the latest romset and put it in the directory for 86Box called roms\
3. Download DOS 3.2 image disks here.
4. Download Windows 1.01 image disks here.
5. [For later fun: download any of the other amazing images on the parent page]
6. Start 86Box and set up 86Box by selecting Tools->Settings from the top menu, and set the system up with the following settings.

Part 2: DOS 3.2 and Windows 1.01 install

1. Start up the 86Box.
2. Set Media->Floppy 1 to disk01.img, then issue a ‘CTRL-ALT-DEL’ to reset it. The system should start up and boot to the dos 3.20 floppy drive
   

1. Run ‘fdisk’ and it should detect your hard drive. You’ll need to create a partition to set up the hard drive.

1. Reboot and boot from the DOS 3.20 disk again.
2. Format the hard drive by using ‘format c: /s’
3. Set Media->Floppy 1 to ‘DISK1-SETUP.IMG’ from the Windows 1.01 (5.25)
4. [optional] type ‘set prompt=$p$g’ if you want to see your full path in the command prompt
5. Run ‘setup’ from a: and follow the instructions to install Windows 1.01 on C:. Change the disks when prompted by selecting Media->Floppy 1 and setting it to each of the floppy disks for the Windows setup until it’s completed.
6. type ‘C:’ to switch to the hard drive
7. ‘cd \windows’
8. ‘win’ to start windows
9. Voila!