Mac Outlook 2011 clients getting bad password prompt in every 15 to 20 minutes

I worked with one of the client last week, they had one strange issue with all of there Mac 2011 outlook clients.

As per the client Outlook 2011 started getting the prompt since last few days and prior to this they were working fine.

They had only three Mac Clients and the same mailbox was working fine when using Outlook 2007 and OWA without any issues.

Environment:
Windows Server 2008 SP2
Exchange Server 2007 SP2 with latest Rollup Updates.

We recreated the profile and it worked for around 30 minutes and failed again with the error above error message.
As Outlook and OWA was working fine correctly i didn't thought of that it could be anything else. Moved the mailbox into another Mailbox Database and checked the issue, and guess what it worked fine for another 30 minute and got the same popup again.
If i click on No and reopen the client than it works fine for sometime and give the same error message.
We had total three outlook 2011 clients on Mac and rest of them were using Outlook 2007.

Removed the EWS VirtualDirectory and recreated the EWS VirtualDirectory New-WebServicesVirtualDirectory and the issue got resolved.

Cheers,
-Gulab

7 Responses to Mac Outlook 2011 clients getting bad password prompt in every 15 to 20 minutes

  1. Anonymous says:

    Hello Gulab

    Please can you advise the procedure to remove the EWS VirtualDirectory and recreate it? where is this done.

  2. Gulab says:

    You need to do it from Exchange Management Shell.

  3. Anonymous says:

    thank you !!

  4. Anonymous says:

    So if I don't have the support of my IT team, am I completely out of luck with this issue? My IT dept does not support Mac applications. I am a user in the field.

  5. Gulab says:

    You will have to run those commands from Exchange Management Shell only. There is no other way. Do you have permission on Exchange Server?

  6. How do i solve duplicate emails from Outlook for Mac 2011? Is there a way to enable Debug logging?

  7. Gulab says:

    Hi Harihara,

    You mean to say, you are getting duplicate emails or you got old dupliate emails?
    For old duplicate emails, this article will fix the issue
    http://support.microsoft.com/kb/2434502

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