I totaly can't configure outlook anywhere. Please help!

I have Exchange 2013 server (both CAS and MBX roles) and another server with NAT (no proxies at all).

I configured outlook anywhere with my internal CA certificate, and install root CA certificate to the external machine. The problem is outlook keep asking for credentials and don't accept them. I tried to configure negotiate and NTLM authentication methods, but it is not help.

https://testconnectivity.microsoft.com/ say all right, except certificate (because it's from internal CA of course), but when i run RCA tool from external PC, it give an error: "Host mail.ko4evneg.ru couldn't be resolved in DNS ErrorRetry". I feel like the problem is in DNS, but nslookup successfully resolve this host. Also I tried to change DNS servers to googleDNS 8.8.8.8 in NIC settings. After that nslookup still successfully resolved host, but RCA gave the same error.

Where shoul I searching for solution? Where RCA get DNS servers, which can't resolve this hostname?

Hi Ko4eveG,

For outlook anywhere two important factor needed.

1. External Hostname for Outlook Anywhere

2. External hostname in the Public Certificate

The External hostname which are used in the Outlook anywhere in Exchange 2013 need to be published in the internet DNS server. So that this should get resolved when you try to access them from internet.

The External hostname should be added as the SAN in your public certificate.

After perfroming then verify by performing the test on right click outlook - Test Email Configuration - Select Autodiscover.

Then check you are getting the XML file generated. Trace the value for EXHTTP protocol in the xml configuration file.

I solved a part of an issue. Just tryied to configure client using autodiscover and it works. 

• Edited by Ko4evneG 17 hours 16 minutes ago

Hi,

According to your description, your Outlook Anywhere clients dont prompt credential any more.
I think the issue may be caused by that it needs time to sync.

And the error in RCA tools is caused by that its an internal certificate not a public one.

If you have any question, please feel free to let me know.
Thanks,