SBS 2008 Exchange Out of Office Not Working

Hello.  We are running an SBS 2008 with Exchange.  Email works fine.  When I activate the OOO message, everything saves fine and the settings seem to be ok.  OWA and Outlook 2010 both show that the OOO is active.  yet no message is generated.  I've checked the settings in the Exchange Console and the OOO is on and set to send external messages.  I've checked the log files and can see all the regular emails going out but nothing ever for the OOO.

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Have you confirmed this is occurring for all users?  Does OOO message not generate for messages sent from internal and external recipients?
bobbydall2000Author Commented:
Yes, same issue for all users and neither internal or external work.
Run the Synchronization, Notification, Availability, and Automatic Replies from and see what if anything is reported.
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bobbydall2000Author Commented:
See results:

Exchange Web Services synchronization, notification, availability, and Automatic Replies.
       Not all tests of Exchange Web Services tasks completed.
      Additional Details
Elapsed Time: 22561 ms.
      Test Steps
      The Microsoft Connectivity Analyzer is attempting to test Autodiscover for
       Testing Autodiscover failed.
      Additional Details
Elapsed Time: 22560 ms.
      Test Steps
      Attempting each method of contacting the Autodiscover service.
       The Autodiscover service couldn't be contacted successfully by any method.
      Additional Details
      Test Steps
Can you run the autodiscover test now.  Is your internal DNS for auto-discover resolving properly?
Simon Butler (Sembee)ConsultantCommented:
Has it ever worked?
Do you have a trusted SSL certificate on the server?

I would start by running the fix my network wizard from the SBS console and see what that comes up with.
Also download the SBS BPA (links on ) and see whether that flags anything of interest.

The primary reason this doesn't work is an SSL certificate error, or DNS resolution.
The fact that Autodiscover externally doesn't work shouldn't affect you internally - unless the clients are all external to the SBS server.


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bobbydall2000Author Commented:
Hi.  I will try the SBS BPA and run the fix my network wizard.  I will do this tomorrow night late after all staff have gone.
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