Hi Jethro,
Compare the hosted mode launch configuration classpath to the libraries that you've deployed with your application on Tomcat to see if there are any missing libraries, specifically the one containing the org.apache.digest.Digester class.
I also noticed that you're using the Gilead project. There are differences between the libraries you need at compile-time and in production, so I suggest you consult the Gilead documentation (link below) to make sure that you've met all the libraries that need to be present in both modes and haven't included extra libraries that may not be needed for deployment.
Gilead project dependencies:
-Sumit Chandel