I have fiddler v5.0.20173.50948
I was recently migrated at work to Outlook 2016 (version 16.0.9001.2080) and an Office 365 mailbox.
When fiddler is active and capturing traffic, I will periodically (approximately every half hour or so) have Outlook attempt authentication, only to pop a dialog that says
"You'll need the internet for this"
with an error code of 0xCAA70004
and outlook will no longer function, unless I turn off fiddler capture & restart Outlook.
I am capturing and decrypting HTTPS traffic, but only for the hosts related to my work as a developer. I tried to relax filters to see all HTTPS traffic and I don't see where fiddler is getting in the way of Outlook.
I have tried disabling IPv6 (tools / options / general), and the steps on http://toenailclippings.idealworld.net/2016/10/we-are-unable-to-connect-right-now/
Neither have worked. Thanks for the help.