My problem i think is simple , but i cannot find the docs to assist me in this. I have my web server responding on the primary interface of my server. However i would like Tomcat to make any outgoing requests ( JavaMail session access, transports, specifically ) initiate throught the second interface/ip on my server. I cannot find a place to specify this in the Properties that I pass to the session factory instance or in the Tomcat server.xml configuration ... etc. It defaults to the primary ip ( the 0 interface ), how can I override this to use a different interface/ip for outgoing communication intiated by my WebApp as opposed to the IP that it responds to requests on. Help. My Web Serv   More>>