stvs thank you for playing with land mines. Really support for wine taking Linux native paths for EXE's would be wise to delete and force the use of Windows Paths. winepath provides you with a means to converting to windows paths. Wine cannot process the command line after the executable to convert from Linux path format to Windows for the application. Reason some applications require flags done /? and the like. Basically the failure you are seeing is perfectly normal and its miss using wine to have the failure. Code: /home/base_dir\sub_dir\file.dat This is caused by something so simple. reader.exe is passed to wine as /home/base_dir/reader.exe Path is extracted from that. /home/base_dir then added to where it wants it file. Correct solution is wine Z:\\home\\base_dir\\reader.exe Yes you missed drive letter.