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.