External Autodiscover error Exchange 2010
Posted on 2016-10-04
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 (184.108.40.206 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 220.127.116.11
- autodiscover IN CNAME 18.104.22.168
-_autodiscover._tcp IN SVR 0 443 server.mydomain.com
Using mxtoolbox.com, the CNAME returns autodiscover.mydomain.com as connected and the IP as 22.214.171.124.
Does anyone see something tragically wrong with what I've done (obviously I've made a mess of this, but please humour me....)?