YouTuber installs Windows on a PSP & it’s baffling

A YouTuber set himself a challenge to install Windows 98 onto the most impractical device he could find – the Sony PlayStation Portable.

One of the major criticisms of handheld gaming devices like the Asus ROG Ally X or the Lenovo Legion Go is how poorly Windows 11 works with the portable form factor.

For some reason, YouTuber and modder Jiga Tech decided that this impracticality did not go far enough, and chose to push the concept straight into the realm of brilliant absurdity.

Jiga had previously modded a 2008 PSP 3000 in a previous video, which involved adding additional software. One of these software applications was DOSBox, a common DOS emulator. This software would be what Jiga would try to use to install Windows 98.

Immediately, Jiga ran into a problem. The PSP lacks any way of plugging in a keyboard. So, Jiga was forced to consult a guide in order to use various button combinations to simulate keyboard inputs.

After copying the install files to the correct directory on the PSP, Jiga began the process of installing Windows on the PSP via DOSBox. The first couple of attempts results in an ‘error loading user.exe’ message.

The process was extremely difficult, with Jiga running into issues with drive letters, various error messages, and at one point, DOSBox crashing and causing the PSP to lock up entirely.

To resolve the assorted problems, Jiga went back and forth between the PSP and his PC, creating various drive images in order to create something that the PSP was capable of loading.

After encountering a seemingly insurmountable problem with Windows 98, Jiga switched from Windows 95, which also did not work, before finally settling on Windows 3.1.

The PSP finally made it to the boot screen, and Windows 3.1 booted. Sadly, it couldn’t do anything else.

Jiga gives up at this point, telling his audience “Can you run Windows 98 on a PSP? Absolutely not.”