It may not be Outlook that's causing the problem. It may be an Add-in to Outlook. Try going to Tools; Options; Other; Advanced; Add-In Manager. One at a time uncheck the things listed, close and restart Outlook.
Every single time I close Outlook I receive an error message and a request to send Microsoft the information. I have not been able to rectify the problem by using office repair or reinstalling office entirely. At this point, the only issue is getting rid of these annoying error messages and requests to send info. Is there a way to disable or turnoff the request to send info to Microsoft window?