I wonder if everyone with this issue has a Dell?
This was found today and we are a Dell shop - we are going to disable the network part of Dell Optimizer on some of the affected machines now and see what happens...
https://www.dell.com/community/Precision-Mobile-Workstations/ExpressConnect-Outlook-Issue/td-p/8199238
ExpressConnect/Outlook Issue
The Dell Optimizer update that was released at the end of April is causing issues with Outlook in our environment. I'm just writing this to hopefully save others some grief if this occurs elsewhere.
After the upgrade, Outlook will either disconnect every few hours or get stuck at loading profile. The only way to resolve it is to restart the PC. This has happend on Precision 5760 & 7550 models as well as Latitude 7420. Uninstalling ExpresConnect from the Add/remove programs applet resolved the issue for several in our environment.
Just hoping that if anyone else has this issue this will help. It took me about 7 hours to figure out what was causing it!