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Failing Auto Configure of Outlook

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  • Hello,


    I have added a new domain to office 365 and am trying to configure users for it. I can create new mail boxes, and the users can login using OWA no problem. However when I try to configure outlook, it is failing to detect the settings.


    I went to www.testexchangeconnectivity.com to do some Office 365 tests for Outlook Autodiscover, and don't really understand the issue.


     Attempting to contact the Autodiscover service using the HTTP redirect method.
      The attempt to contact Autodiscover using the HTTP Redirect method failed.
     
     Test Steps
     
     Attempting to resolve the host name autodiscover.domain.co.uk in DNS.
      The host name resolved successfully.
     
     Additional Details
     Testing TCP port 80 on host autodiscover.domain.co.uk to ensure it's listening and open.
      The port was opened successfully.
     ExRCA is checking the host autodiscover.domain.co.uk for an HTTP redirect to the Autodiscover service.
      The redirect (HTTP 301/302) response was received successfully.
     
     Additional Details
     Attempting to test potential Autodiscover URL https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml
      Testing of this potential Autodiscover URL failed.
     
     Test Steps
     
     Attempting to resolve the host name autodiscover-s.outlook.com in DNS.
      The host name resolved successfully.
     
     Additional Details
     Testing TCP port 443 on host autodiscover-s.outlook.com 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
     Checking the IIS configuration for client certificate authentication.
      Client certificate authentication wasn't detected.
     
     Additional Details
     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 https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml for user thomas@domain.co.uk.
      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).

    The error at the end states that I am getting an 401 Unauthorized due to incorrect username / password / UPN.


    At first I thought it may have been a UPN issue, so I checked in powershell, and it is correct.


    UserPrincipalName                       DisplayName                             isLicensed
    -----------------                       -----------                             ----------
    thomas@domain.co.uk       Thomas                             True


    I know the username / password is correct, as I can login fine to OWA.


    Can someone help me out?


    Thanks


    Elliot


  • Just wanted to add some extra information.

    I created user 1 and then deleted it, and recreated it. I did not do a restore.

    User 1 cannot use the autodiscover.

    If I create a new user, user 2, the auto discover works for that user. So I think it's something with accounts that have been created, deleted and then recreated.

    Perhaps this will let you point me in the right direction?

  • Hi ElliotK,

    Before moving on, I want to confirm with you for the following information.
    1, Which Outlook Client version you use, Outlook 2010 or Outlook 2007?
    2, Have you ever try to connect via manual configuration?
    3, Due to your description, only user1 you have recreated has the auto discover issue, user2 auto discover works fine, and both the two account can login OWA, is it correct?

    Based on the current situation, I suggest you connect the Outlook via manual configuration to see if it works.
    Moreover, after you delete a user mailbox, and then recover it, the Exchange Online Server may take some time to recover the mailbox.
    Reference
    =========
    http://support.microsoft.com/kb/2404385

    Thanks,
    Eric Sun

  • Hi ElliotK,

    How are you doing? Is there any information update?
    I am just writing to see if there is any progress on this issue. I do not mean to push you. I just want to ensure that you do not encounter any problems during the troubleshooting. Thank you.

    Cheers,
    Eric Sun

  • I have this working now.

    I had to move user1 to user1.new then restore the previously deleted user1. I then changed user1 to user1.old deleted it, and moved user1.new back to user1.

    I think this is a bug. If you delete an account, you can then create another account with the same username, which doesn't work properly. When creating accounts it should also check deleted accounts that are available for restore.

    Hope this helps someone in the future.

    Thanks

  • Hi ElliotK,

     

    I’m glad to hear that the issue has been resolved, and thank you for your sharing. If you have any question about Office365 you can post them here/in the forum.
    Have a good day!

    Thanks,
    Eric Sun

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