Hi there
1) As you've mentioned the authentication I use is domain\username and password. I also cleared all cached credentials and tried again with no avail.
2) Here are the results for the remote connectivity analyser:
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for "email address".
Testing Autodiscover failed.
Additional Details
Elapsed Time: 3947 ms.
Test Steps
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
Additional Details
Elapsed Time: 3947 ms.
Test Steps
Attempting to test potential Autodiscover URL https
Testing of this potential Autodiscover URL failed.
Additional Details
Elapsed Time: 1492 ms.
Test Steps
Attempting to resolve the host name domain.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: xxx.xxx.xx.xxx
Elapsed Time: 227 ms.
Testing TCP port 443 on host domain.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 378 ms.
Testing the SSL certificate to make sure it's valid.
The SSL certificate failed one or more certificate validation checks.
Additional Details
Elapsed Time: 885 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server domain.com on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: OU=Domain Control Validated - RapidSSL(R), OU=See, OU=GT14623739, SERIALNUMBER=XLjzfa7swZZElnkDNb4XkkTNhKV6F1a9, Issuer: CN=RapidSSL CA, O="GeoTrust, Inc.", C=US.
Elapsed Time: 861 ms.
Validating the certificate name.
Certificate name validation failed.
Tell me more about this issue and how to resolve it
Additional Details
Host name domain.com doesn't match any name found on the server certificate - RapidSSL(R), OU=See (c)12, OU=GT14623739, SERIALNUMBER=XLjzfa7swZZElnkDNb4XkkTNhKV6F1a9.
Elapsed Time: 0 ms.
Attempting to test potential Autodiscover URL autodiscoverdomaincom443/Autodiscover/Autodiscover
Testing of this potential Autodiscover URL failed.
Additional Details
Elapsed Time: 1486 ms.
Test Steps
Attempting to resolve the host name autodiscover.domain.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: xxx.xxx.xx.xxx
Elapsed Time: 289 ms.
Testing TCP port 443 on host autodiscover.domain.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 336 ms.
Testing the SSL certificate to make sure it's valid.
The SSL certificate failed one or more certificate validation checks.
Additional Details
Elapsed Time: 859 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover.domain.com on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=HOST, Issuer: CN=HOST.
Elapsed Time: 836 ms.
Validating the certificate name.
Certificate name validation failed.
Tell me more about this issue and how to resolve it
Additional Details
Host name autodiscover.domain.com doesn't match any name found on the server certificate CN=HOST.
Elapsed Time: 0 ms.
Attempting to contact the Autodiscover service using the HTTP redirect method.
The attempt to contact Autodiscover using the HTTP Redirect method failed.
Additional Details
Elapsed Time: 833 ms.
Test Steps
Attempting to resolve the host name autodiscover.domain.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: xxx.xxx.xx.xxx
Elapsed Time: 7 ms.
Testing TCP port 80 on host autodiscover.domain.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 281 ms.
The Microsoft Connectivity Analyzer is checking the host autodiscover.domain.com for an HTTP redirect to the Autodiscover service.
The Microsoft Connectivity Analyzer failed to get an HTTP redirect response for Autodiscover.
Additional Details
An HTTP 403 forbidden response was received. The response appears to have come from Unknown. Body of the response:
HTTP Response Headers:
X-FEServer: HOST
Content-Length: 0
Date: Thu, 25 Jun 2015 11:28:21 GMT
Server: Microsoft-IIS/8.5
X-Powered-By: ASP.NET
Elapsed Time: 544 ms.
Attempting to contact the Autodiscover service using the DNS SRV redirect method.
The Microsoft Connectivity Analyzer failed to contact the Autodiscover service using the DNS SRV redirect method.
Additional Details
Elapsed Time: 80 ms.
Test Steps
Attempting to locate SRV record _autodiscover._tcp.domain.com in DNS.
The Autodiscover SRV record wasn't found in DNS.
Tell me more about this issue and how to resolve it
Additional Details
Elapsed Time: 80 ms.
I'm sure the results of this points clearly to a few things that might be the root of the problem, certificate and autodiscover?