SSL mail not sending thru Outlook 2002

I'm running Outlook 2002 and win2k. I've set up a SSL email account. When I test the settings in the e-mail accounts set up everything works fine. However, when I try and send an e-mail it simply does not send and times out. If I change the outgoingparameters to a normal (ie normal port 25 and normal unsecure server) SMTP setting then it works fine. I've put all the correct settings in and triple checked them and still am not able to send.