In what is quite a major achievement, Wine has been ported and made to work on OpenBSD.
We have since tested several dozens of 64-bit Windows software, mostly successfully. See screenshots, livestream recordings for example. Even the Remaster of The Witcher 3 which released just last month runs, and runs well (requires adding in vkd3d-proton; see README; livestream which looks less fluent than it is due to the on-system recording with ffmpeg).
↫ Thomas Frohwein
The biggest limitation seems to be the lack of support for WoW64, so 32bit Windows software won’t work. Still, this is a massive milestone for OpenBSD, and makes especially gaming a somewhat viable option on OpenBSD.
SYSWOW64 isn’t going to happen for the same reason 32-bit i386 Wine won’t happen. It requires user-level setting of processor descriptor tables, which OpenBSD fundamentally disallows for security reasons.
FlyingJester
I didn’t know that OpenBSD doesn’t support 32bit code, but it should be noted that user space software does not actually require access to descriptor tables, it’s the OS that manages the descriptor table. If OpenBSD doesn’t already have it, then It will require some new 32bit trampoline kernel interface, but nothing insurmountable. The bigger question is likely whether 32bit Wine is valued enough to justify adding 32bit to OpenBSD.
Also, 32bit Wine requires a complete 32 userspace tree, which is a lot of effort.