I had some problems with running rake under cygwin. I get the following error while trying to execute rake:C:\Ruby192\bin\ruby.exe: No such file or directory – /cygdrive/c/Ruby192/bin/rake (LoadError) Could it be that the problem is that the first line in rake:#!/usr/bin/env ruby  Will return C:\Ruby192\bin\ruby.exe By being more explicit about what to run you can avoid the problem:rake.bat