As you can see port 587 works fine without SSL, but...

SMTP Server Settings

SMTP Server and port: Enter the SMTP Server Address. You can also specify an alternate port by adding a colon and the port number (e.g. smtp.googlemail.com:587). Enter the SMTP server name only to use default port number (25)	Test Email Sent Successfully
SMTP Authentication: Enter the SMTP Server Authentication method ( default = Anonymous )	Anonymous Basic NTLM
SMTP Enable SSL: Used for SMTP services that require secure connection (usually not needed)
SMTP Username: Enter the Username for the SMTP Server
SMTP Password: Enter the Password for the SMTP Server

but... If I change the port to 465 and select SSL (and repaste the password for good measure); update; test; I get this:

SMTP Server Settings

SMTP Server and port: Enter the SMTP Server Address. You can also specify an alternate port by adding a colon and the port number (e.g. smtp.googlemail.com:587). Enter the SMTP server name only to use default port number (25)	Test There has been an error trying to send the test email. The error is: The operation has timed out.
SMTP Authentication: Enter the SMTP Server Authentication method ( default = Anonymous )	Anonymous Basic NTLM
SMTP Enable SSL: Used for SMTP services that require secure connection (usually not needed)
SMTP Username: Enter the Username for the SMTP Server
SMTP Password: Enter the Password for the SMTP Server

I have tried this on my Outlook 2007 without problems on either.  I am using EasyDNS's EasySMTP service because that is where I have my MX record managed and I want the email recipients email servers to be able to do their due diligence for spam control.  If I go through Shaw, they will likely be black listed and unless they manage my MX record, I don't think spam controllers will see me as legitimate.

Sure, I could do it without SSL, but I want to know what I am doing wrong!  Please help.