A port proposal posted to the openbsd-ports mailing list brings Wine to OpenBSD. The sticking point had been %gs/gsbase, which OpenBSD does not let userland set. The workaround emulates the %gs prefix on instructions in software, and that opened the way for the rest of the port.
Several dozen 64-bit Windows programs have been tested, mostly working. The Witcher 3 remaster, released last month, runs with vkd3d-proton added. The main limitation is that WoW64 does not work, so 32-bit Windows software will not run at all. Check a binary with file(1): if it reports a 32-bit Intel 80386 PE, it is out. The built-in test suite is disabled for now because the tests need an X server and several hang.
The post suggests Notepad++ as a small 64-bit program to try first. It also recommends running Wine as a separate unprivileged user, with unveil(2) fencing still an open question.…