TLDR: Winbox 3.27 (64-bit) + CrossOver Mac = ✅
today I tried Apple Silicon (Winbox 3.27-64bit, Big Sur 11.0.1, Rosetta + Homebrew 2.5.11 + wine64 5.7). I can run Winbox fine, but there is at least one glitch. Winbox window can't be resized. Maybe something with xquartz. There is no such glitch on Intel based Big Sur. I tried wine-stable 5.7 and wine-staging 5.7 with the same result.
# Aliases alias intel="arch -x86_64" alias winbox="arch -x86_64 wine64 /Applications/winbox64.exe" # Mikrotik Winbox export PATH="/Applications/Wine Staging.app/Contents/Resources/wine/bin:$PATH" export FREETYPE_PROPERTIES="truetype:interpreter-version=35" export DYLD_FALLBACK_LIBRARY_PATH="/usr/lib:/opt/X11/lib:$DYLD_FALLBACK_LIBRARY_PATH"