Since you are using Tiger, you'll need to install x11 from the Tiger Install DVD. It's the Optional Installs.mpkg file. And you may need to start wine with: Code: DYLD_FALLBACK_LIBRARY_PATH=/usr/X11/lib wine ./my.exe The drag and drop method you describe definitely works most of the time, but some applications must be run from the directory. using your example: Code: cd /Users/michaelrivera/Desktop/ARENA10Softwarepack wine setup.exe should work for you.