Quote Originally Posted by ne0dym View Post
It's funny that the official client wouldn't work but my own Wine wrapped version does lmao.
Eh, not really that odd. Crossover is a tweaked, optimized version of Wine, and moreover probably one derived from a version of Wine later than installing wine-stable from Homebrew on High Sierra will get you. In particular, Crossover (and Wine in general) needed a bunch of changes to support running 32-bit Windows executables on a 64-bit-only operating system (i.e. Catalina), so they did all kinds of stuff to make the graphics pipeline theoretically more powerful while in there. Unfortunately, all those upgrades also bumped the base version of MacOS required, presumably because (as witnessed above) some of those changes didn't work right on older systems.

Wrapping it in the base version of Wine that you did is basically like taking the current client and stuffing it into an older build of Crossover; on an old system, wholly viable. On a 64-bit-only system like Catalina or Big Sur, though, running the old version would simply fail. And I'm guessing they came down on the side of Catalina and Big Sur support being higher priority to them than continuing to support anything prior to Mojave.