Here is a second thing to try openssl dgst -sha1 /Users/Username/.winetrickscache/./WindowsXP-KB975337-x86-ENU.exe The result should be similar to this (updated to your path): windows@jmd0 ~ $ openssl dgst -sha1 /home/windows/.winetrickscache/WindowsXP-KB975337-x86-ENU.exe SHA1(/home/windows/.winetrickscache/WindowsXP-KB975337-x86-ENU.exe)= b9a84bc3de92863bba1f5eb1d598446567fbc646