Torquebox and Cygwin don’t work as nicely together as one might hope. That said, here are a couple of findings: In order to deploy, you need to set the $JBOSS_HOME with the Windows path. You can do this via export JBOSS_PATH=cygpath -w PATH_TO_JBOSS. Additionally, the JRUBY_HOME needs to be a windows path as well. Otherwise …