Selected mail not delivered

This is on Exchange 2007. I have a group of users that are unable to send emails to a certain domain from within Outlook. However if they use OWA then the emails are delivered to that domain without problem. All email originating from the problem domain and sent to us are delivered without problem. Both businesses are my clients so I have access to both Exchange servers for troubleshooting. I have tried whitelisting our domain on the target domain's exchange server but that has not helped. There has never been any non-delivery errors generated at either end. Also we have a second group of users on our exchange server. They have a different reply to domain. Those messages are being delivered to the problematic domain without any problems.

I am completely at a loss to explain why a subset of our users would be unable to send to a domain from their desktop while at the same time have the ability to send from OWA. I had originally thought it was a filtering issue based on the different reply to domains but whitelisting the domain did not help and as I said they users are able to send using OWA.

Anyone have any suggestions on how to troubleshoot this? I am not even sure which server I should be looking at for the problem.
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pmckenna11Asked:
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AeridenConnect With a Mentor Commented:
Are NDRs setup to occur on both Exchange Servers?  Meaning, if the domain is mydomain.com, and someone sends to notanemailaddress@mydomain.com, would they get an NDR?

Have you tried turning on Message Tracking (especially, initially, on the sending side)?  http://www.msexchange.org/tutorials/Exchange-2007-Message-Tracking-Part1.html
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OctInvConnect With a Mentor Commented:
Is the CAS server (for OWA) the same server as the hub transport server?
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pmckenna11Author Commented:
Yes the OWA is on the hub transport server (both sites are using SBS2008 with Exchange 2007). Given that they are on the same server, I can't begin to fathom why emails sent directly from Outlook would fail while they work fine from OWA.  I need to check the NDR settings. I had assumed that it was turned on by default by maybe not. I will check into the message tracking link and gather more information and post back. Thanks for the help so far
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