Had the same problem. Followed the same guide to a T, and grabbed assorted and sundry simple exe files, installs and straight executables, and had the same problem. wine: Bad EXE format for Z:\Users\.... The build was flawless from what I observed. This was supposed to be a trial go. The first attempt generated more information: wine: created the configuration directory '/Users/carya/.wine' fixme:system:SetProcessDPIAware stub! fixme:dwmapi:DwmIsCompositionEnabled 0x33c534 fixme:file:MoveFileWithProgressW MOVEFILE_WRITE_THROUGH unimplemented fixme:advapi:SetNamedSecurityInfoW L"C:\\windows\\system32\\gecko\\1.0.0\\wine_gecko\\components\\xpti.dat" 1 536870916 0x0 0x0 0x1ff564 0x0 fixme:iphlpapi:NotifyAddrChange (Handle 0xa73f518, overlapped 0xa73f520): stub fixme:file:MoveFileWithProgressW MOVEFILE_WRITE_THROUGH unimplemented fixme:advapi:SetNamedSecurityInfoW L"C:\\windows\\system32\\gecko\\1.0.0\\wine_gecko\\components\\compreg.dat" 1 536870916 0x0 0x0 0x1d352c4 0x0 fixme:event:wait_for_withdrawn_state window 0x1005c/c00001 wait timed out fixme:event:wait_for_withdrawn_state window 0x20070/a00001 wait timed out wine: configuration in '/Users/carya/.wine' has been updated. err:module:map_image Could not map section .text, file probably truncated err:module:map_image Could not map section .text, file probably truncated wine: Bad EXE format for Z:\Users\.... I looked around in .wine/ (being new to this and all) and saw : lrwxr-xr-x 1 carya staff 10 Oct 13 06:28 c: -> ../drive_c lrwxr-xr-x 1 carya staff 1 Oct 13 06:28 z: -> / Looked in all the other files in that directory and nothing stood out as a source of a glitch other than possibly configurations that weren't customized properly. Any advice on where to go from here would be helpful. At the very least now I have ports working, whereas it wasn't before, and I have the latest XQuartz and all of XCode installed now. Thanks in advance.