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.

Read the rest of this entry »

Outlook 2016 bug for POP accounts

Recently, we’ve had quite a few customers write in to complain that their copy of Outlook 2016 is behaving incorrectly: it is either deleting messages from the server when it is not supposed to do so, or it is downloading duplicate copies of mail from the server. This happens for POP accounts, not for IMAP accounts (which is what we normally recommend customers to use).

These problems happen because of a bug in Outlook 2016. Microsoft has a Web page that explains the problem as well as the solution (upgrade Outlook).