Running Windows 3.11 on a Raspberry Pi can be done using emulation. This will cover how to use an emulation utilitiy called DosBox. This post (https://youtu.be/idHQk99E4VA), from Christopher Barnatt inspired me to dust off my old floppy disks and give it a go. You can find more here as well, http://explainingcomputers.com/

Sourcing Windows 3.11 can be challenging. I have 6 install disks that were part of my college computer, an AST i486SX 33Mhz CPU with 8MB of ram and a 256MB hard disk (circa 1994). That computer cost me $1200 and put me in more debt that I should have while attending school. However, it became a learning experience.

Some of my disks have not aged well, so I was able to source installation media from this website, https://www.kirsle.net/msdos. Now that the installation disks are available, I’m ready to start.

On my Raspberry Pi, I’ll need to install DosBox. This is done issuing this command in a terminal windows.

sudo apt-get install dosbox

Now DosBox should be installed and the next step is to copy the Windows 3.11 install files to the Raspberry Pi. Following Christopher’s example, I created a folder called “Pi_C” to place the Win311 files into. Just a reminder, this legacy system will only support 8.3 file conventions. If you place folders or files with long names, they will be truncated.

Next, DosBox can be started and the Pi_C folder mounted. Once DosBox has been started, mount the folder by entering in these commands in the DosBox dialog window.

mount c Pi_C
c:
cd <your win 311 directory name here>
setup

This will not only mount the folder in DosBox, but also change to the install directory and start the windows 3.11 installation. Finish the installation, reboot, and you should have windows 3.11 installed and ready to run.

It’s amazing to look back at the technology and how it has progressed over the years. The Raspberry Pi 3 has over 145 times the processing power of my AST i486SX computer. The ram and file system space on the Raspberry Pi have a similar ratio. To put it in cost perspective, it would have cost over $150,000 to match the processing power of the $40 Raspberry Pi.