SSL-Related Timeouts and Port 45
You are getting timeout-related failures and are using port 465
Many mail providers instruct their users to use port 465 with SSL as the Connection Type. This usually indicates that the mail provider has port 465 set up for “implicit SSL”. SoftRAID’s email notification system only works with “explicit SSL” or TLS, both of which are usually configured on port 587. All of the mail providers that we have experience with offer one of the following:
both implicit and explicit SSL
try changing to port 587.
if you are still having trouble, check with your mail provider’s outgoing SMTP settings to see what other outgoing ports they offer.
If you are still having problems, contact SoftRAID Support, and we will work with you to fix the issue.
If you are interested in more information about implicit vs. explicit SSL, the team at Fog Creek Software wrote a succinct post explaining this issue as it relates to the email notification feature in product FogBugz: http://help.fogcreek.com/9002/using-an-smtp-server-with-ssl