I have the same problem with the "time out operation" after the port is set to 465 and the SSL is checked, but I spoke with my host administrator and he saw that when I try to send email from my own domain it is secure (because I own SSL certificate) and I can use port 25 without concerns. That is why it can't manage to make secure connection, because (if I understood correctly) it is internal and safe (you send emails from the server where you website is hosted).