Having trouble with Outlook 2011 for Mac and SSL?
A couple of customers have recently contacted us about problems with Outlook 2011 for Mac when it’s configured to make SSL connections.
Outlook 2011 for Mac has a bug: It tries to use the long-obsolete “SSLv2” protocol that is no longer supported on modern mail servers, including ours. If your network also uses a very common kind of firewall that prevents “client-initiated SSL/TLS session renegotiation”, SSL connections will simply fail.
The best solution to this is to upgrade to a modern version of Outlook. Outlook 2016 for Mac, for example, doesn’t have this problem.
If you can’t do that, you can make it continue to work by turning off “Use SSL to connect” and making sure the incoming and outgoing ports are correct, as shown on our page about Outlook 2011 settings.
In theory, turning off SSL encryption in the Outlook settings weakens security, making it possible for attackers who have access to your network to intercept your password. In practice, SSLv2 has not been secure for many years, and offers little protection against attackers anyway. You should update to the current version of Outlook if you are concerned about security.