I hadn’t logged into outlook sync in a while so I ran some tests to see if I had any issues logging in, and outside of my password being out of date in the autofill, I was able to log in with no SSL/TLS error. I didn’t see any reports in the recent cases. You may want to give our support team a ring when you have a little time @ 1-866-800-0004 Ext 2. They have a few steps to work through, and the ability to enable some logging to see if we can pinpoint the problem. If they are unable to find the issue off hand, they should be able to present the data up to our Advanced Support team.
If you are still experiencing this, give our support team a ring when you are around a computer that has the plug-in running.