If you want to capture issues that occur when Outlook starts or issues with Autodiscover, then you need to restart Outlook once logging was enabled. Once logging is enabled, you should reproduce the issue and then disable logging by returning to Errors window and switching off logging option. How to enable logging Outlook 2011 for Mac
In Outlook 2016 for Mac version 15.12.3 and later versions, there is an additional list of features that are also logged: Microsoft Exchange (folder and item synchronization).
Outlook for Mac gives an ability to capture behavior of the following Outlook features: This article shows how to enable logging in Outlook 2011 for Mac and Outlook 2016 for Mac.
