Calendar Revisions not sending resulting in NDR

We're experiencing an issue that doesn't seem to happen very often, so it's been difficult to troubleshoot. We've had an issue with a user sending out updates to calendar invites and it never making it resulting in an NDR.

When running message tracking, this is what we get

Date Time SMTP Store Driver: Message Submitted from Store
Date Time SMTP: Message Submitted to Advanced Queuing
Date Time SMTP: Started Message Submission to Advanced Queue
Date Time SMTP: Message Submitted to Categorizer
Date Time SMTP: Message Catergorized and Queued for Routing
Date Time SMTP: Message Routed and Queued for Remote Delivery
Two Days Later SMTP: Non-Delivery Report (NDR) Generated

So we're missing the line for SMTP: Started Outbound Transfer of Message.
The following line would normally show transferred message to server.domain.com through SMTP. We are using an encryption gateway setup as a smart host. All other email is flowing through properly. This just randomly seems to be an issue. This has also only happened to one person that I know of. Previously this was with sending to a gmail account. Now this is a private domain that this is happening. All other mail and original calendar invites are flowing properly. This is just calendar updates. This was also the case for the gmail issue.

We are running Exchange 2003 fully patched. Email comes into the organization through a spam firewall, and out from the exchange server to an encryption gateway and to the real world.

Please let me know if you need any further information.
Thanks, Ryan.
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RyrenAsked:
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Jamie McKillopIT ManagerCommented:
Hello,

This hotfix should resolve your problem - http://support.microsoft.com/kb/938650/en-us

JJ
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RyrenAuthor Commented:
JJ --

Thank you very much for your response!

I will apply this hotfix and let you know how this goes.

The only question I have is why this would happen on gmail accounts as well? I haven't confirmed that the end user currently being sent to is using Exchange 2007 and I don't know that I will be able to. Would this fix still be relevant if they're not using Exchange 2007?
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Jamie McKillopIT ManagerCommented:
I'm not sure about about gmail. The KB article is specific to Exchange 2003 sending to Exchange 2007.

JJ
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RyrenAuthor Commented:
Right -- being specific between 2003 and 2007 is what promted the question. I can not be sure the user we're sending to is using Exchange 2007 (They're actually a customer) and I'm pretty sure gmail isn't using exchange 2007, and being this issue has been present in gmail as well, I'm wondering whether it's something else. With that said, I'm going to research this update and apply it. If you can think of anything else this would be, please let me know.

This has been a lonely question for a couple of days. I'm hoping to get a couple of other eyes on this. Thanks for your help!
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Jamie McKillopIT ManagerCommented:
The issue definately exists between Exchange 2003 and Exchange 2007, so i would recommend applying the hotfix in any case. Can you post the actual NDR you are receiving?

JJ
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RyrenAuthor Commented:
Your message did not reach some or all of the intended recipients.

      Subject:      Manual Discussion and Suggestions

The following recipient(s) cannot be reached:

      Users Name (88) on 7/2/2009 11:32 AM
            Could not deliver the message in the time limit specified.  Please retry or contact your administrator.
            <server.domain.com #4.4.7>

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Jamie McKillopIT ManagerCommented:
That's the same NDR I've seen that is resolved with the hotfix.

JJ
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RyrenAuthor Commented:
Excellent -- I will apply this hotfix and ask the user to resend the update and see if this rectifies the situation. I will also see if by chance this fixes the gmail issue as well..

Thanks, JJ. I'll update you shortly.
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RyrenAuthor Commented:
JJ -- That did fix the issue. This resolved the problem with gmail as well.

We're good to go. Thanks for your help!
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