What are you, nuts?

Pretty much. I was born in the nineties, and the first personal computer my family bought (a $3000 screamer with a 300 MHz Pentium II, 256 MB of RAM, and the optional Boston Acoustics speaker system) ran Windows 95. Also, this isn’t the first time I’ve installed an old operating system on a watch. Here’s a video of my Apple Watch running Mac OS 7.5.5:

But How?

Unlike the above port of the Mini vMac emulator, the result here had to be interactive. That meant that Apple’s WatchKit SDK wasn’t good enough, since it doesn’t allow you to access user touch locations directly — it only lets you use Apple’s stock controls. Long story short, it’s possible to patch certain files within a WatchKit app to load your own application code rather than Apple’s. For more information, check out Steven Troughton-Smith’s excellent blog post on the subject.

Here’s an outline of the steps involved:

Copy symbols and headers from Xcode’s iphoneOS and iphoneSimulator platforms to the watchOS and watchSimulator platforms, respectively.

Build your “normal” UIKit-based iOS app inside a framework, rather than in your WatchKit extension.

Use install_name_tool to point your WatchKit app’s _WatchKitStub/WK binary to your framework instead of SockPuppetGizmo. SockPuppetGizmo is the framework that (to my knowledge) runs WatchKit and interacts with normal WatchKit extensions that developers write.

binary to your framework instead of SockPuppetGizmo. SockPuppetGizmo is the framework that (to my knowledge) runs WatchKit and interacts with normal WatchKit extensions that developers write. Jury-rig the iOS port of the Bochs x86 emulator into your framework. “Easy!” “How hard can it be?” read: Pretty hard. In my case, Xcode crashed whenever I tried to use lldb. Your mileage may vary.

Copy a Windows 95 disk image in to your app’s bundle, write the config file, and boot ‘er up.

*Optional: hot glue a motor to the watch’s crown to keep it from falling asleep.

Will It Blend?

Yes! Due to the fact that it is emulated (not virtualized), it takes about an hour to boot.