Office 365 Migration with Cisco IronPort

I ran across an interesting issue recently where a client could not get Autodiscover to work properly during their “rich coexistence” period with an on-prem Exchange 2010 during their migration to Office 365. Autodiscover for an on-prem user would work fine, but as soon as the user had their mailbox moved to Office 365 the Autodiscover process wouldn’t work. The DNS records looked fine and when looking at the log we saw the client would connect to the internal SCP, get a redirect to Office 365 for the correct SMTP address, and then fail. We couldn’t set up a brand new profile for the user internally, but we noticed it would work perfectly ok from an Internet client. Must be something internal at that point, right?

After some more testing we learned a Cisco IronPort was being used for outbound web proxy filtering. As soon as we added an exception for the test machine's IP address we found Autodiscover worked just fine for a cloud user. In the end we added an exception for the FQDNs and Secure web filtering keeping users safe and admins frustrated. Happy migrating.