The best solution to this is to upgrade to a modern version of Outlook.
If your network also uses a very common kind of firewall that prevents “client-initiated session renegotiation”, SSL connections will simply fail.
Outlook 2011 has a bug handling SSL connections: It tries to use the long-obsolete “SSLv2” protocol that is no longer supported on modern mail servers, including ours. You're finished! Try sending yourself a test email message to make sure it works.
