I am using windows 10, and outlook 2016. I installed Fiddler and configured it for WinHttp and SSL and everything worked fine. My internet settings are set to automatically detect proxy settings and I followed the documented settings for WinHttp configuration ("netsh winhttp set proxy netsh winhttp set proxy 127.0.0.1:8888 "<-loopback>"). As I mentioned, I was able to see all traffic. The first strange thing that happened is that Outlook stopped working unless Fiddler was running. If Fiddler was not running, I get just get disconnected message from Outlook. I changed the WinHttp settings back, (netsh winhttp set proxy default) but the issue did not go away. I tried changing the Fiddler SSL settings to just connect for browsers, but no change. I tried to not connect to SSL at all, and unchecked the box which started fiddler as a proxy, but still no change. I uninstalled Fiddler, but Outlook is still broken. I went in and deleted the Fiddler cert but still nothing. I am sure this is not a coincidence as I previously encountered this and rebuilt the system. This is the second time I have seen this same behavior, only after installing and using Fiddler. Any ideas how to fix it?