I've setup ispconfig3 on my debian six server, and here is a little smtp over ssl:
The server is postfix
AUTH PLAIN (LOL!)
235 2.7.0 Authentication successful
MAIL FROM: lol@lol.com
250 2.1.0 Ok
RCPT TO: lol@lol.com
RENEGOTIATING
depth=0 /C=AU/ST=NSW/L=Sydney/O=Self-Signed Key! Procees with caution!/OU=Web Hosting/emailAddress=postmaster@lol.com
verify error:num=18:self signed certificate
verify return:1
depth=0 /C=AU/ST=NSW/L=Sydney/O=Self-Signed Key! Procees with caution!/OU=Web Hosting/emailAddress=postmaster@lol.com
verify return:1
DATA
554 5.5.1 Error: no valid recipients
but, the thing is, if I just do a vanilla telnet over port 25 I can authenticate and send mail like a madman... hopefully this is enough information! (as opposed to 'mail.app can't handle ssl!')