Print Queue - Port 465 Problem

All,

I am getting a problem in connecting to my smtp server through port 465 - Log output:

<Event Timestamp="2013-04-25T20:23:00.1891+00:00" Level="ERROR" Identity="Guest"><Message>Error sending email to recipient(s) 'matt@mattblackler.com'. System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 

 

   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)

 

   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)</Message></Event>

After doing some reading, it appears that secured email traffis (ssl/tls mail) is not supported by the system.net.mail library.

Is this the case?  What do other people do in this instance?

Regards,

Matt