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Exchange email is showing up 'To' someone but is only delivered to the users 'CC'ed on it

kittensizedbulldozer
on
Medium Priority
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Last Modified: 2008-03-10
So I need to figure out if this is a problem with our Exchange Server or the other company we're partnered with. I think it's on their end, but I may have overlooked something. Consider the following scenario, breathe deeply, and don't let it drive you to the madness it's driven me over the past couple of days. :)
I'm running Exchange Server 2003 Enterprise w/ SP2 and Intelligent Message Filtering turned on. It's on a Windows 2003 Enterprise Server box.
The following takes place:
H.R Rufflestein at Partner Company sends my boss an email, and CC's a few people. The people CC'd on the email receive it, but my boss who's in the 'To' field does not.
My boss has two emails, Boss.Lastname@mycompany.com and Bossnickname@mycompany.com. If H.R Ruffestein sends to Boss.Lastname@company.com, my boss gets it just fine. If it's sent to Bossnickname@mycompany.com, it's not delivered. There is no NDR generated as far as I can tell (ie, H.R Rufflestein doesn't get a bounce message.)
Bossnickname@mycompany.com is the primary SMTP address for his account. (He's fond of his nickname)

Now looking at the Outlook headers on the other users' account, in the 'To' field in the headers it shows:

Subject: RE: mail troubles
Date: Tue, 24 Oct 2006 17:12:08 +0200
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
Thread-Topic: mail troubles
Thread-Index: Acb3fSc2ZMNHlnIKScGuqgoWIRSLwAAAWgbQ
From: "H.R Ruffestein" <H.R.Ruffestein@partnercompany.com>
To: "Boss Man" <bossnickname@mycompany.com>
Cc: "KittenSizedBullDozer" <confuseditguy@mycompany.com>

My boss doesn't get this, and I get it showing it 'To' him and CC'ing me. However, in the Exchange Message Tracking Center, the XML generated file shows this:

  <Recipients>
- <Recipient>
  <RecipientAddress>confuseditguy@mycompany.com</RecipientAddress>
  <RecipientStatus>0</RecipientStatus>
  </Recipient>
  </Recipients>
  </Exchange_MessageTrackingEntry>
- <Exchange_MessageTrackingEntry>
  <TimeLogged>2006-10-24 15:14:36</TimeLogged>

In the same XML file, there is no record of my boss' email being anywhere in the Recipients tags.

So here's the question: Is this being stripped off or blocked somehow at our end, or is this being blocked at their end? My hunch is it's on their end, but I want to make doubley sure I'm not missing something on my end. Thanks in advance.
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Expert of the Year 2007
Expert of the Year 2006

Commented:
Diagnosing delivery problems as the recipient is almost impossible as there are any number of places where the message could be dropped.

The remote site needs to prove the message was delivered. If they cannot, then there is little that you can do.

Message tracking just shows you what Exchange has received. If the message has never been received by the Exchange server then Message Tracking can't show you anything.

Simon.
Well, ok, so how to I determine if the problem is occuring at my end?
Is there a better way to be diagnosing the mail traffic issue? It's interesting to me that I would receive the message and the other user would not.
My hunch is, as I mentioned, it could be occuring on their end, but I'm certainly open to it being a configuration problem on mine.
Thanks!
Expert of the Year 2007
Expert of the Year 2006
Commented:
Not a lot you can do. The other end has to prove either that the message was delivered or provide an NDR. Until the message actually hits your server you have no way of knowing what is happening to it. As the recipient, you can do nothing.

For example, the sending party could try a telnet test to your server to that email address to see if the manual message is delivered or not. The telnet test would allow them to see that they have connected to your server.

You have no way of knowing how the outbound email from that remote site is sent - it could be directly to your server, through one or more third party servers, through servers at their ISP etc.

Simon.

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Ok I understand that part. Thanks!
Now, is there anyway to log every message that's sent to one user? What I'd like to do now is log every message sent to my boss into a log file in order to track and see if on the chance these messages are arriving, that it's not then somehow being filtered by IMF or if it's disappearing into some obscure obsoleted filter in Outlook.

Or should I ask this as a seperate question and award points now?
Expert of the Year 2007
Expert of the Year 2006

Commented:
Message tracking already does that. If you want to retain the log longer just increase the days.
Then when it comes to tracking their messages simply adjust the filter in the message tracking centre to see what Exchange did with the message.

If Exchange is filtering the message then it will show in the tracking log. Similarly if the message is hitting the mailbox then being filtered by something client side (ie in Outlook) then the tracking log will show the delivery and then you can investigate the client.

Simon.
Thanks Simon I appreciate the help.
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