Can't connect to exchange via Outlook, works via OWA RRS feed

  • Question

  • Hello,

    I've recently installed SBS 2008, and configured Exchange 2007. I can log in via Outlook Web Access, and send/receive emails both internally and externally with no problems. I've managed to get the autodiscover functioning yesterday, and also properly configured my DNS settings so that autodiscover is, well, discoverable. Everything was functioning perfectly last night, and I ran the Outlook Anywhere and the Outlook Autodiscover tests last night on in order to verify that everything was alright; after the tests were ran, and everything passed, I figured I was finished with messing around with my Exchange server. 5 hours later, for no apparent reason at all, I couldn't connect to my exchange server via outlook at all, with the exception of one account, which would be the test account I created under my name. Nothing special was added to the account. It was just a simple Network Admin account I made via SBS console. I've ran into a few errors, and I've done a lot of research, but to no avail.

    I tried creating another account last night for testing purposes, and everything was set up properly, with the exception of the Exchange welcome email not being able to be sent to my inbox. I dove in a little deeper, and found this error:


    An account failed to log on.
      Security ID:    NULL SID
      Account Name:    -
      Account Domain:    -
      Logon ID:    0x0
    Logon Type:      3
    Account For Which Logon Failed:
      Security ID:    NULL SID
      Account Name:    Sean
      Account Domain:    Seanpc
    Failure Information:
      Failure Reason:    Unknown user name or bad password.
      Status:      0xc000006d
      Sub Status:    0xc0000064
    Process Information:
      Caller Process ID:  0x0
      Caller Process Name:  -
    Network Information:
      Workstation Name:  SEANPC
      Source Network Address:
      Source Port:    58886
    Detailed Authentication Information:
      Logon Process:    NtLmSsp
      Authentication Package:  NTLM
      Transited Services:  -
      Package Name (NTLM only):  -
      Key Length:    0
    This event is generated when a logon request fails. It is generated on the computer where access was attempted.
    The Subject fields indicate the account on the local system which requested the logon. This is most commonly a service such as the Server service, or a local process such as Winlogon.exe or Services.exe.
    The Logon Type field indicates the kind of logon that was requested. The most common types are 2 (interactive) and 3 (network).
    The Process Information fields indicate which account and process on the system requested the logon.
    The Network Information fields indicate where a remote logon request originated. Workstation name is not always available and may be left blank in some cases.
    The authentication information fields provide detailed information about this specific logon request.
      - Transited services indicate which intermediate services have participated in this logon request.
      - Package name indicates which sub-protocol was used among the NTLM protocols.
      - Key length indicates the length of the generated session key. This will be 0 if no session key was requested.


    I've tried the DisableLoopbackCheck via registry, and that didn't fix it. I tried the wininternals idea someone else had regarding changing the SID, and that didn't work either. I'm not entirely sure that these errors are related to my issue of not being able to connect via Outlook, but I figured I'd post them here just incase.


    I just need to be able to connect to my server via Outlook, and the fact that my server now fails all of the Exchange connectivity tests when I didn't change a single thing also boggles my mind. Any help would be appreciated.


    Thank you.




    Jay Tabatabai
    Thursday, April 21, 2011 10:20 PM

All replies

  • As it is SBS, the first thing to do is run the Fix My Network wizard in the management console. Then run the SBS BPA (free download from Microsoft) and ensure that doesn't flag anything.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Thursday, April 21, 2011 10:40 PM
  • I have tried your suggestion, the Fix My Network wizard fixed three problems, and the SBS BPA didn't flag anything, but I still can't connect via outlook to my exchange server. Any other suggestions?

    Jay Tabatabai
    Friday, April 22, 2011 1:48 AM
  • Hi Jay,

    "I couldn't connect to my exchange server via outlook at all"

    What's the error message when you connect to Exchange?

    Suggest you install the latest service pack and rollup in order to avoid some known issues first.

    Will this post be helpful?

    Outlook 2007 asks for password when using Exchange 2007

    Frank Wang

    TechNet Subscriber Support in forum

    If you have any feedback on our support, please contact  

    Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
    Friday, April 22, 2011 8:23 AM
  • Hello Frank,


    I tried the above suggestions (and also read the thread + tried what others have said), and it is still repeatedly prompting me for user name/password. Any other suggestions?


    edit: Outlook doesn't give any errors. It just continues to prompt me for a user name and password. The user name and password works perfectly fine via OWA.

    Jay Tabatabai
    • Edited by jaytaba Saturday, April 23, 2011 12:14 AM
    Friday, April 22, 2011 9:38 PM
  • Frank, I've ran a diagnostic report for you as well.



    Please tell me if you need anything else.

    Jay Tabatabai
    Friday, April 22, 2011 11:38 PM
  • Hi Jay,

    I'm research the issue. Please wait. Thanks.

    Frank Wang


    Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
    Tuesday, April 26, 2011 2:28 AM
  • Hello Frank,


    I appreciate the help. This problem has been bugging me for almost 2 weeks now. It's weird how Outlook doesn't work, but Outlook Web Access functions normally.

    Jay Tabatabai
    Tuesday, April 26, 2011 7:06 PM
  • Hi Jaytaba,

    Does it work consistently with admin accounts? In other words, have you tried creating a couple of test admin accounts and giving them full domain admin/exchange admin rights to see if they are able to login?

    Also, what happens if you change the authentication method in the Outlook profile to use NTLM instead of Kerberos?

    Have a look at the following article that explains why i'm asking this, and how to modify the profile to use NTLM:

    927612 You are repeatedly prompted to enter your credentials when you try to connect to an Exchange mailbox by using Outlook 2007;EN-US;927612

    These are 2 different directions (test accounts and modifying the profile)... but 1 leans towards a permission/policy issue and one towards SPN records...


    Kevin Ca - MSFT
    Monday, May 9, 2011 1:05 AM