Linux/wine

sudo dpkg --add-architecture i386
sudo apt update
sudo apt install --install-recommends winehq-staging

Rebuild Wine Prefix (~/.wine)
 wineboot -u

Test new wine prefix:
 WINEPREFIX=~/my_new_prefix wine your_executable.exe

Test wine with executable:
 xvfb-run -a wine your_executable.exe

Reconfig your wine prfix:
 rm -rf .wine
 winecfg
 # or if headless...
 xvfg-run wincfg