System.Net.Mail supports "explicit SSL" (also known as "StartTLS" - usually on port 25 or 587), but not "implicit SSL" (aka "SMTPS" - usually on port 465).
As far as I know, explicit SSL is started from an insecure connection, then the STARTTLS command is issued, and finally, a secure SSL connection is created. Implicit SSL, on the other hand, requires an SSL connection to be configured before both parties begin to speak.
Some servers (e.g. gmail) accept both, so you just need to set EnableSsl to true and send to the right port. If your server does not support explict SSL, this "easy way" is not an option.
I am also still considering a general solution for using System.Net.Mail with implicit SSL, without knowledge.
Anyway, look in this article , this may give you some idea.
[edit: @ Nikita is right, fixed port numbers to avoid confusion]
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