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Autodiscover problems in Exchange 2016

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  • Autodiscover problems in Exchange 2016

    Hello all,

    I have successfully migrated a single node Exchange 2010 to a Two-node DAG Exchange 2016. A quick look of our environment is as below:

    Different IInternaland External Domains
    External Domain name:
    Internal Domain name:

    Servers fully qalified names:

    A wild card certifacte contains both domain names and both Server names.

    Internal DNS has two enteries of Autodisocver: - pointing to Server 1 - pointing to Server 2

    I am however, having some problems with Autodiscover. The Outlook behaves strangly, it sometimes keeps prompting for the password and does not take you anywhere. Other times even a cancel button works fine. The connection status changes from "Need Password" to "Disconnected" and then Connected. Clearing the Credential does not help.

    Exchange Connectivity test gets passed with the following errors:

    Attempting to test potential Autodiscover URL
    Testing of this potential Autodiscover URL failed.

    Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
    Autodiscover settings weren't obtained when the Autodiscover POST request was sent.

    The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL for user ..........
    The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.

    Additional Details

    A Web exception occurred because an HTTP 404 - NotFound response was received from IIS7.
    HTTP Response Headers:
    Content-Length: 4888
    Cache-Control: private
    Content-Type: text/html; charset=utf-8
    Date: Tue, 17 May 2016 00:51:19 GMT
    Server: Microsoft-IIS/8.0
    X-Powered-By: ASP.NET
    Elapsed Time: 617 ms.

    Any help shall be greately appreciated. Thanks