Currently I have IIS 6.0 (on Windows 2003) running the redirector plug-in which is directing Tomcat requests to a separate physical server running Tomcat 5.5.17 on Windows 2003. Currently the redirector plug-in is successfully forwarding JSP requests (from configuring the workers.properties file) from the IIS server to the Tomcat server. When a client browser connection makes a request through IIS, IIS serves the site URL correctly on HTTP or HTTPS BUT when IIS forwards requests (due to the filter configuration) to Tomcat currently via HTTPS (SSL) (JSSE) is not working. The server running Tomcat has J2SDK 1.4.2_6 and JRE 1.5.0_07 installed and I pointed JSSE_HOME to the JRE 1.5.0_07 directory since its copy of jsse.jar is newer. I have successfully added a certificate to the keystore (“certificate was added to keystore”). I have edited the server.xml with connector settings: <Connector port="8443" maxThreads="150" minSpareThreads="25" maxSpareThreads="75" enableLookups="true" disableUploadTimeout="true" acceptCount="100" debug="0" scheme="https" secure="true" clientAuth="false" sslProtocol="TLS" keystoreFile="D:\apps\Tomcat 5.5\conf\tomcat.keystore" keystoreType="JKS" keystorePass="mypassword"> </Connector> When I attempt the following URLS to test SSL, I receive the following errors. http://localhost/secure - I receive a 404 https://localhost:8443 – page cannot be displayed What else can I do to verify all the JSSE components are all present and working? Can anyone put me back on the path to encryption? I must figure out how to have IIS forward SSL/HTTPS requests to Tomcat and have Tomcat serve the requests via SSL/HTTPS. Any help is much appreciated. Edward