Outlook Plugin - Crashing

Hello Everyone, 

We seem to be having some problems with our Sugar Outlook plugin. When outlook is initially opened, sugar plugin will be stuck in "connecting" indefinitely. 

In order to bypass this message, you need to try and Sync an Email manually, to get this message: 

Click Cancel, so that the web page verification pops up, and then click allow. 

It will then connect. 

Even when connected I still find myself hitting the "archive to sugar" button manually, as emails will not automatically push over to sugar. 

Once I am finished manually syncing all of my emails, the first email I try to send from outlook, will ALWAYS crash the application and I am forced to restart, and the hole cycle starts again. 

Obviously these challenges do not make for a very friendly workflow. Has anyone else experienced these issues?