I am not sure if this may be causing the problem here. When I ping autodiscover (netbios format) from the Outlook client computer it resolves to the INTERNAL active directory DNS name and not the external/internet accessible domain that is published in the URL fields. The exchange 2010 server is configured as the recipient for autodiscover, which in this case is named as ‘’ versus the traditional ‘’ that is typically used. There is an entry of ‘autodiscover’ as an A record in the DNS *local* zone pointing to the Exchange 2010 server (no load balancing on the 2010 environment).
Now I am little unclear based on the current DNS configuration if this may be contributing to the problem: So I can only assume that somewhere I have the incorrect URL specified, but I have the externally published autodiscover address specified for all URL fields (as far as I can tell). If I change this field to the autodiscover address and recheck the name, it immediately works. When allowing Outlook to go through the auto-configuration process, the server name field keeps defaulting to the Netbios server name of the mailbox server hosting the users mailbox. The user accounts in question can successfully access their mailboxes through OWA. Outlook must be online or connected to complete this action” when creating a new fresh profile from an Outlook 2013 client. I am experiencing the dreaded “The connection to Microsoft Exchange is unavailable. Working through an Exchange 2010 to 2016 migration and struggling to understand why am I experiencing the following behavior while connecting Outlook clients to mailboxes on new Exchange 2016 server.
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