In reference to ticket #4803225, Outlook would connect from inside the domain and on slower networks such as a mobile hotspot, but not from faster home networks. It is still unclear as to why this was happening but a workaround was found. There is a checkbox in the Microsoft Exchange Proxy Settings which can be found by going to File->Account Settings->Change Account Settings->More Settings->Connection Tab->Exchange Proxy Settings. Enable the check box for "On fast networks, connect using HTTP first, then connect using TCP/IP" See attached image for reference. You will have to restart Outlook after making this change.