I should note this is my first major Exchange project.
We're preparing to migrate to Office365 but found that Autodiscover is critical to the migration. It works fine internally, but externally we've never had much success.
OWA works fine internally and externally, and Exchange Active Sync works fine on hundreds of devices in the organization, however running the connectivity test reports the following:
ttempting to test potential Autodiscover URL https://autodiscover.mydomain.com/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Additional Details
Elapsed Time: 1112 ms.
Test Steps
Attempting to resolve the host name autodiscover.mydomain.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 68.249.X.X
Elapsed Time: 96 ms.
Testing TCP port 443 on host autodiscover.mydomain.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 107 ms.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Additional Details
Elapsed Time: 383 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover.mydomain.com on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=mail.mydomain.com, OU=Domain Control Validated, O=mail.mydomain.com, Issuer: SERIALNUMBER=mySN, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O="GoDaddy.com, Inc.", L=Scottsdale,
S=Arizona, C=US.
Elapsed Time: 303 ms.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name autodiscover.mydomain.com was found in the Certificate Subject Alternative Name entry.
Elapsed Time: 1 ms.
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
Test Steps
The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=mail.mydomain.com, OU=Domain Control Validated, O=mail.mydomain.com.
One or more certificate chains were constructed successfully.
Additional Details
A total of 1 chains were built. The highest quality chain ends in root certificate OU=Go Daddy Class 2 Certification Authority, O="The Go Daddy Group, Inc.", C=US.
Elapsed Time: 31 ms.
Analyzing the certificate chains for compatibility problems with versions of Windows.
Potential compatibility problems were identified with some versions of Windows.
Additional Details
The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Elapsed Time: 4 ms.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 6/29/2011 7:36:36 PM, NotAfter = 6/29/2016 7:36:36 PM
Elapsed Time: 0 ms.
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Elapsed Time: 291 ms.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
Additional Details
Elapsed Time: 232 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.mydomain.com/AutoDiscover/AutoDiscover.xml for user administrator@mydomain.com.
The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
Additional Details
An HTTP 500 response was returned from Unknown.
Headers received:
Content-Length: 75
Content-Type: text/html
Date: Tue, 18 Mar 2014 18:13:11 GMT
Server: Microsoft-IIS/7.5
HTTP Response Headers:
Content-Length: 75
Content-Type: text/html
Date: Tue, 18 Mar 2014 18:13:11 GMT
Server: Microsoft-IIS/7.5
Elapsed Time: 232 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: 206 ms.
Test Steps
Attempting to resolve the host name autodiscover.mydomain.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 68.249.65.82
Elapsed Time: 15 ms.
Testing TCP port 80 on host autodiscover.mydomain.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 76 ms.
The Microsoft Connectivity Analyzer is checking the host autodiscover.mydomain.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 500 response was returned from Unknown.
Headers received:
Content-Length: 75
Content-Type: text/html
Date: Tue, 18 Mar 2014 18:13:12 GMT
Server: Microsoft-IIS/7.5
HTTP Response Headers:
Content-Length: 75
Content-Type: text/html
Date: Tue, 18 Mar 2014 18:13:12 GMT
Server: Microsoft-IIS/7.5
Elapsed Time: 115 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.mydomain.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: 79 ms.
Checking if there is an autodiscover CNAME record in DNS for your domain 'mydomain.com' for Office 365.
Failed to validate autodiscover CNAME record in DNS. If your mailbox isn't in Office 365, you can ignore this warning.
Tell me more about this issue and how to resolve it
Additional Details
There is no Autodiscover CNAME record for your domain 'mydomain.com'.
Elapsed Time: 66 ms.