I am currently in the middle of a migration from Ex2010 to Ex2013 and I have hit a wall that I cannot seem to get around. The environment consists of one Ex2010 server (all roles installed) with one mailbox database and one public folder database and two new multi-role Ex2013 servers (one in the primary AD site with the Ex2010 server and one in our DR AD site). I have a split-DNS configuration with all virtual directories on both sides pointed to mail.corp.com and autodiscover.corp.com. The SSL cert on my Ex2010 server is still valid for a while so I exported that and imported it to the new Ex2013 servers with no trouble. I am able to pull up the new Ex2013 ECP and manage the new Ex2013 environment.
If I leave my DNS for mail.corp.com pointed to the Ex2010 server, I can fire up an Outlook 2016 client and I can create a new profile for a Ex2010 mailbox. I can then close out Outlook, edit my local hosts file to point mail.corp.com and autodiscover.corp.com to my new Ex2013 server, and when I launch Outlook, it is still able to open the Ex2010 mailbox. I can also do the same thing using OWA. When I first browse to OWA, it comes up using the new Ex2013 interface and when I enter my credentials, the mailbox opens in the old Ex2010 OWA interface so it is definitely using proxy via the Ex2013 server.
My problem begins when I edit my local hosts file to point to the new Ex2013 server but I don't have an Outlook profile created yet. In that case, Outlook 2016 opens and I enter in the name for the profile. On the next screen, my user name and email address auto-populate so that part is good. But as soon as I click Next and the "Configuring" window shows up, I see that "Establishing network connection" passes, but then I get stopped at "Searching for user@corp.com settings" and then a credentials box pops up. I am planning to migrate all mailboxes over from 2010 to 2013 in the very near future so I don't know how much to worry about this problem. i am concerned that if I press on and migrate the mailboxes, that I may end up running into other problems later so I would like to solve this problem if possible.
I have gone through numerous tech notes and went back and forth on different authentication methods and IIS auth methods for both servers. Currently, on Ex2013, I have ExternalClientAuth and InternalClientAuth both set to NTLM and IISAuth set to Basic, NTLM, and Negotiate. On Ex2010, I have ExternalClientAuth and InternalClientAuth both set to NTLM and IISAuth set to Basic, NTLM. On Ex2013, I do see that I have ExternalClientRequireSSL and InternalClientRequireSSL both set to True while on the Ex2010 side, ExternalClientRequireSSL is set to True and InternalClientRequireSSL is set to False. Perhaps that is the problem?