troubleshooting Question

External Autodiscover error Exchange 2010

Avatar of Philip Thomas
Philip Thomas asked on
ExchangeOutlookDNS
5 Comments1 Solution161 ViewsLast Modified:
I have been working with Microsoft to set up a Federation Trust between my company's 4 domains. 2 are Exchange 2010 hosted on-premise, and 2 are seperate tennants in Exchange 365. First they directed me to set up a Hybrid configuration, which did nothing but waste time. After escalating my request, a tech tested everything internally (which I had set up properly from the start), and on the 365 side, only to tell me there was an issue that they couldn't pinpoint and that I should contact the Exchange 2010 support team. I'd rather try with you all first, so here goes:

When I run the Outlook Connectivity test on testconnectivity.microsoft.com I am getting the following errors:

*Testing the SSL certificate to make sure it's valid.
       The SSL certificate failed one or more certificate validation checks.
   >Validating the certificate name.
       Certificate name validation failed.
      >Host name mydomain.com doesn't match any name found on the server certificate CN=css.mydomain.com

*Attempting to test potential Autodiscover URL https://autodiscover.mydomain.com:443/Autodiscover/Autodiscover.xml
       Testing of this potential Autodiscover URL failed.
   > Host autodiscover.mydomain.com couldn't be resolved in DNS InfoDomainNonexistent

*Attempting to contact the Autodiscover service using the DNS SRV redirect method.
   >Attempting to resolve the host name server.mydomain.com in DNS.
      >The host name couldn't be resolved.

In my public DNS, I've just added autodiscover.mydomain.com as an A record, and it is pointing to the same server as my OWA (which works) record (1.2.3.4 for this example).

For myself, this is a needle in a haystack kind of problem. I've added the following records in my public DNS:

- autodiscover.mydomain.com IN A 1.2.3.4
- autodiscover IN CNAME 1.2.3.4
-_autodiscover._tcp IN SVR 0 443 server.mydomain.com

Using mxtoolbox.com, the CNAME returns autodiscover.mydomain.com  as connected and the IP as 1.2.3.4.

Does anyone see something tragically wrong with what I've done (obviously I've made a mess of this, but please humour me....)?
ASKER CERTIFIED SOLUTION
Todd Nelson
Systems Administrator

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