I have an exchange 2003 enviroment with one back-end server and one perimeter server (gateway server). I am trying to setup smtpS on the gateway server I have created two virtual smtp servers there one using port 25 (smtp) and one using port 465 (smtpS) but when users try to connect using smtpS it just keeps prompting them for their password like as if they are not authenticated. They are able to use the smtp with no problems. I do have good certs applied to the servers and at this point I am really stumped as to what could be causing the problem. Does anyone have any experience setting up smtpS could you give me any pointers or suggestions things I may need to look at? thanks for any help!

See if this helps. There are some nice screenshots if you scroll down: http://www.isaserver.org/img/upl/exchangekit/2003securesmtpsmtps/2003securesmtpsmtps.htm