Working in support at Microsoft, you get to deal with a lot of organizations who are migrating to Exchange Online. This type of migration dramatically changes how web traffic flows in the organization as the traffic moves away from Exchange on the Local Area Network to servers hosted by Microsoft in a Microsoft Data Center, essentially a remote internet location. We spend plenty of time troubleshooting Outlook when a customer has difficulties connecting to their Office 365 mailbox. We troubleshoot other connectivity issues too of course, and we continually use tools such as The Support and Recovery Assistant (SARA), (top support tip: particularly useful to detect client based issues is the Collect Information about my Outlook configuration option in SARA) Outlook ETL files (which can only be viewed by Microsoft support), and Fiddler traces to see the conversation between the Outlook client and the service – whether that’s Exchange Online, some other Office 365 service, or an Authentication or Federation provider. Since we spent so much time working with Fiddler, we wanted to put together an extension which brings our knowledge of the issues we see on a daily basis directly into Fiddler to assist with troubleshooting Outlook and Exchange Online. Whether you are in contact with Microsoft support or otherwise, we’re putting it out there so you can use it too!
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