What was the system you tested this on originally? Mojave?
I'm on MacOS 11 Big Sur Beta(Will try Catalina tomorrow, doubt it'll make a difference), but I cannot get Halo 2 to run using Wine 2.9.0.6-1, WS11WineCX64bit19.0.1-1 as WS9/WS10 won't even launch to start the install). All I get is the...