I have successfully redirected from IIS 5 to Tomcat 5.5 the /serlvet-examples webapp that comes with the Tomcat 5.5 distribution. I also have been able to successfully test my own servlets by calling them directly on port 8080. I have been unable, however, to redirect to these servlets in the same fashion as the sample servlets. When I view the uri runtime info via /jkstatus everything looks consistent so I suspect the workers2.properties file listed below.
#Look at #http://jakarta.apache.org/tomcat/tomcat-4.1-doc/jk2/jk2/configwebcom.html #for parameter description
# Uri mapping [uri:/jkstatus/*] worker=status:status
Let me reiterate that everything works fine by calling port 8080. All servlets located in /servlets-examples work. A servlet in /sample works but a jsp file in that webapp throws a HTTP 500 - Internal server error as well as all of the servlets in the /contracts webapp.