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Outlook 2011 for Mac prompts for exchange password and then fails to sync even though outlook initially syncs

    Question

  • We are having an issue with Outlook 2011 for Mac clients connecting to our Exchange 2010 SP1 server.
    the server settings are configured properly, after launching outlook 2011 for Mac, the initial sync seems to work fine.  However, after 2 minutes or so Outlook 2011 asks to allow the autodiscover URI to configure the account.  After this it asks for the username and password.  We are 100% sure that we have correct credentials.  The following log entries show up in the troubleshooting log.

    [     2403us, d       584us] Outlook Exchange Auto Configure: Querying https://cas.domain.name/autodiscover/autodiscover.xml
    [     2432us, d        29us] Outlook Exchange Auto Configure: HTTP send message failed with error code: 401
    [     2432us, d         0us] Outlook Exchange Auto Configure: === Failed to retrieve autodiscover settings for user@domain.name

    My first thought is that this was an authentication method issue.  Here is the results of our autodiscover virtual directory config query:

    RunspaceId                      : 8cb0da41-c4fc-4f36-aafa-e46bc9fb60ca
    Name                            : Autodiscover (Default Web Site)
    InternalAuthenticationMethods   : {Basic, Ntlm, Digest, WindowsIntegrated, WSSecurity}
    ExternalAuthenticationMethods   : {Basic, Ntlm, Digest, WindowsIntegrated, WSSecurity}
    LiveIdSpNegoAuthentication      : False
    WSSecurityAuthentication        : True
    LiveIdBasicAuthentication       : False
    BasicAuthentication             : True
    DigestAuthentication            : True
    WindowsAuthentication           : True
    MetabasePath                    : IIS://mbx.domain.name/W3SVC/1/ROOT/Autodiscover
    Path                            : C:\Program Files\Microsoft\Exchange Server\V14\ClientAccess\Autodiscover
    ExtendedProtectionTokenChecking : None
    ExtendedProtectionFlags         : {}
    ExtendedProtectionSPNList       : {}
    Server                          : MAIL
    InternalUrl                     : https://cas.domain.name/autodiscover/
    ExternalUrl                     : https://cas.domain.name/autodiscover/
    AdminDisplayName                :
    ExchangeVersion                 : 0.10 (14.0.100.0)

    Note that I've obviscated server and URLs for security reasons.  However SSL certificates are installed at the appropriate endpoints.

    Note that this same user is able to be confirmed as working by the microsoft exchange connectivity test tool.  With settings discovered using autodiscover.  Windows Outlook 2007 and 2010 clients work flawlessly with this same account.

    Anyone have any idea what might be causing this?

    Any help would be appreciated.
    Thanks!

     

    • Changed type P. Bossley Monday, December 27, 2010 7:24 PM
    Monday, December 27, 2010 6:07 PM

Answers

  • Hi P.Bossley,

    Do all Mac clients have the issue?

    Do you have legacy Exchange in the organization?

    Please try to reset the EWS Virtual Directory to test.

    Server Configuration->Client Access->Actions->Reset Virtual Directory->Browse->EWS


    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.
    • Marked as answer by P. Bossley Wednesday, December 29, 2010 2:11 PM
    Wednesday, December 29, 2010 8:26 AM

All replies

  • Hi P.Bossley,

    Do all Mac clients have the issue?

    Do you have legacy Exchange in the organization?

    Please try to reset the EWS Virtual Directory to test.

    Server Configuration->Client Access->Actions->Reset Virtual Directory->Browse->EWS


    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.
    • Marked as answer by P. Bossley Wednesday, December 29, 2010 2:11 PM
    Wednesday, December 29, 2010 8:26 AM
  • Hello,

    Yes, all Outlook 2011 clients on Mac OSX have this issue.  However Apple Mail clients seem to work properly.  There is a legacy Exchange 2003 server in the organization however these mailboxes are brand new (not migrated) from Legacy Exchange.  I will give the EWS directory reset a try later this morning.

     

    thanks for the suggestionn.

    Wednesday, December 29, 2010 12:00 PM
  • Resetting the EWS and autodiscover directories did the trick after re-adding the external and internal URLS.  Thanks for the pointers!
    Wednesday, December 29, 2010 2:14 PM