Trying to execute the program from the terminal reveals that the PATH Wine is using is different from where Wine actually placed the file. mike@mike-desktop:~/.wine/drive_c/Program Files/Broderbund/Calendar Creator$ ls AGB CCSku.dll Creator.exe crown.ico License.txt MSRUN32.EXE Template Unlock Version.txt CATALOG.INF Creator.chm Creator.ico history.txt MSREG.INI Sounds tips.txt UserData.dll mike@mike-desktop:~/.wine/drive_c/Program Files/Broderbund/Calendar Creator$ cd \ > mike@mike-desktop:~$ wine Creator.exe wine: cannot find L"C:\\windows\\system32\\Creator.exe" mike@mike-desktop:~$