Greetings,
I have two Exchange 2013 server inside my organization both running on Server 2012 R2 and both set up with CAS/MBX roles and this system has been up and running for about a year now. This system was deployed as Exchange 2013 from the outset so no other
versions of Exchange have ever been in AD. The system is configured to accept mail for multiple domains. Split-DNS is configured and so from both the inside and outside, everything is referenced by mail.domain1.com. My SSL cert is a SAN-cert
with the issued name as mail.domain1.com and SAN of autodiscover.domain1.com.
Inside, Autodiscover works with no trouble on domain-joined clients as we simply create a new Outlook profile for Exchange and everything populates automatically. We don't have any non-domain clients inside and so I am uncertain as to whether or not
Autodiscover works on those types of clients.
For the past couple of days, I have been trying to make Autodiscover work from the outside on a non-domain-joined client with no VPN connection back to the inside network. When I use the ExRCA, I have success with both the Outlook Autodiscover and
Outlook Connectivity tests. But when I attempt to configure a new Outlook profile, I supply the name, email address and password of the account and I hit next and then I see "Searching for user@domain1.com settings". After about a 30-second
pause, instead of completing the account configuration, I always get taken to a dialogue box with "Windows Security" at the top and then further down it reads "Mail Application" and below that, "Connecting to user@domain1.com"
and then it wants me to supply the account password again. I can seemingly enter the password as many times as I want but this prompt continues to pop up and the account never gets configured.
Since the ExRCA tests are successful, I'm at a loss for what I am missing. I have tried this with both Outlook 2013 and Outlook 2016 and I get the same results. Any tips, hints or suggestions would be appreciated!
D