SMTP Issues - Apple Mail - VERY ANNOYING !

So.

On my iPhone I can connect to my office server, send mail no problem, using port 587, the server address, SSL turned on, with the proper credentials for username and password. When I try to mimic this using the same information on my client end of things, all I get with Apple Mail is the "Connecting to server <xxx.xxx.xxx>" OVER AND OVER AND OVER in the Activity window. All of the ports are properly configured on the router, firewall, etc.. as I am able to send using that SAME SERVER with my phone, and iPad. What gives ? I am pulling my hair out trying to sort this out as it is very frustrating. On the mail server side of things (Kerio Connect) really nothing had changed on the server setup for outgoing mail, and SMTP (port 25, 587, 465) services are configured and ready to go using authentication.

If ANYONE has an information on this, it would be greatly appreciated. Is this a timeout issue ? Is it a handshake issue with the server ? A bit stumped for ideas at this point. Thanks in advance.

I am running 10.7.2 - Mail v5.1 I get the same behaviour on a laptop running 10.6.8

Jeff.