https://bugs.winehq.org/show_bug.cgi?id=49260
--- Comment #10 from Nikolay Sivov bunglehead@gmail.com --- I don't know if it's feasible, but to rule out mac-specific window management issues, you could try to run with winex11 driver + xquartz. It used to work before, not sure how hard it would be to get it running on current macos releases.