Booting a Pi Into Windows 98 (Sort Of)

From the computer-in-a-keyboard design of the Raspberry Pi 400 and 500 that brings back memories of early personal computers to the popularity of RetroPie and Batocera installations for retro gaming arcades, Raspberry Pis seem to be perfectly suited for emulation and nostalgic computing projects. But when these machines boot up a modern Linux operating system, that illusion is broken.

So to keep the retro experience pure, Redditor Anchorboiii figured out how to boot a Raspberry Pi directly into Windows 98. Well, sort of. Windows 98 isn’t exactly going to play nice with a modern ARM chip, but thanks to DOSBox-X, it can emulate the experience quite convincingly. A round of Doom, anyone?

It took a little bit of wrangling to make this possible. A bash script in the autostart folder is triggered on boot, and that immediately launches Windows 98 via DOSBox-X in fullscreen mode. To hide any traces of Raspberry Pi OS, the desktop background was set to pure black, as was the toolbar, which had all items removed from it.

To cover all the bases, Anchorboiii also made a retro Gateway logo that displays while Raspberry Pi OS boots. This hides any remaining traces of the modern system that is actually running behind the scenes.

Anchorboiii doesn’t provide a step-by-step guide, but the process is fairly simple. If you want to run Windows 98 on your own Pi, it shouldn’t be too difficult to make it happen.