Autodiscover not authenticating correctly (Full Version)

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telrick -> Autodiscover not authenticating correctly (18.Nov.2011 3:02:46 PM)

I am using a trial version at the moment.  Trying to get the Autodiscover service to work for iPhones so I can convince the boss to upgrade from 2003.

Running on Server 2008 r2

Single Exchange 2010 server

I ran test-outlookwebservices from the shell, and everything passed.

When I try from I get this output (changed domain and user information):

Attempting to test potential Autodiscover URL
    Testing of this potential Autodiscover URL failed.
   Test Steps
   Attempting to resolve the host name in DNS.
    The host name resolved successfully.
   Additional Details
    IP addresses returned: x.x.x.x
   Testing TCP port 443 on host to ensure it's listening and open.
    The port was opened successfully.
   Testing the SSL certificate to make sure it's valid.
    The certificate passed all validation requirements.
   Test Steps
   ExRCA is attempting to obtain the SSL certificate from remote server on port 443.
    ExRCA successfully obtained the remote SSL certificate.
   Additional Details
    Remote Certificate Subject: <removed>.
   Validating the certificate name.
    The certificate name was validated successfully.
   Additional Details
    Host name was found in the Certificate Subject Common name.
   Testing the certificate date to confirm the certificate is valid.
    Date validation passed. The certificate hasn't expired.
   Additional Details
    The certificate is valid.
   Checking the IIS configuration for client certificate authentication.
    Client certificate authentication wasn't detected.
   Additional Details
    Accept/Require Client Certificates isn't configured.
   Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
    Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
   Test Steps
   ExRCA is attempting to retrieve an XML Autodiscover response from URL for user
    ExRCA failed to obtain an Autodiscover XML response.
   Additional Details
    An HTTP 401 Unauthorized response was received from the remote Unknown server. This is usually the result of an incorrect username or password. If you are attempting to log onto an Office 365 service, ensure you are using your full User Principal Name (UPN).

So, then I tried launching the autodiscover.xml from IIS7.

When browsing to https://localhost/autodiscover/autodiscover.xml, I get the expected http 600 error responce, however, when I browse to internally, I get the username/password popup window, but it will not authenticate me.
I know I am using the correct username/password as I can login to the domain using those same credentials.

The external and internal domain names are not the same.  The user logs into and the email address is  The accepted domain of is set as the default.

When prompted for the username/password, it is defaulting to, which is correct.

Any help will be appreciated.



shanmarsh3 -> RE: Autodiscover not authenticating correctly (17.Dec.2011 4:18:20 AM)

The XML page comes up correctly. Internally and externally does not work.
Body Armour | Safeguard Clothing

jveldh -> RE: Autodiscover not authenticating correctly (19.Dec.2011 5:26:30 AM)


How is the server published to the internet and did you create the A record in the external DNS?


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