from the website intro page: Wine's main task is to run Windows executables under non Windows operating systems. It supports different types of executables: DOS executable. Those are even older programs, using the DOS format (either .com or .exe (the later being also called MZ)). Tried it: fixme:module:__wine_load_dos_exe DOS executables not supported on this platform in thread Execution DOS exe program via Wine ?: Maybe 'wineconsole' (comes with wine) will work better for you. And maybe you need something like dosemu... What's the best way forward on OSX 10.6.8?