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jk connector tomcat 4.1.27

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We have a web application running on tomcat 3.2.4 fronted by Iplanet using the AJP 1.3 jk connector. The tomcat instance is running on "machine_1" and the web server on "machine_2". machine_2 has the domain name foo.com and has ssl turned on.
The welcome file for our application is index.jsp. With tomcat 3.2.4 and the jk connector the application is accessible at both https://foo.com/webapp/ and https://foo.com/webapp/index.jsp.
We wanted to switch to a newer version of tomcat. We shutdown the 3.2.4 instance and configured a 4.1.27 instance using the deprecated jk connector so that we wouldn't have to upgrade/change our web server configuration.
Now with tomcat 4.1.27 everything is redirected properly through https://foo.com/webapp/index.jsp.
However when https://foo.com/webapp/ is hit the redirect doesn't work properly. According to the catalina_log file (we turned debug all the way up) when https://foo.com/webapp/index.jsp is hit the AJP13 connector properly gets the referer as https://foo.com/webapp/index.jsp. However when https://foo.com/webapp/ is hit the referer resolves to https://machine_2.com/webapp/ . The application is served up but instead of https://foo.com/webapp/ in the address bar https://machine_2.com/webapp/ is shown.
Since our security certifcate is for foo.com the user is given a warning that the certifacte is invalid if they use the url https://foo.com/webapp/
This error does not occur if they use the URL https://foo.com/webapp/index.jsp
Again with tomcat 3.2.4 and the jk connector to the web server works fine. Upgraded to 4.1.27 tomcat (and kept the web server the same) and the jk connector only partially works.
Any ideas?
Consider Paul's rocket mass heater.
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