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How it was done...

 

https://medium.com/tendigi-insights/i-installed-windows-95-on-my-apple-watch-589fda5e36d

 

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.
     
  • 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.

 

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

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