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Exchange 2007 oddity

Gregory Miller
Gregory Miller used Ask the Experts™
on
Getting #554 Transaction Failed messages to one recipient host. Working with the recipient server administrator is proving to be more frustrating than it should be. I feel the need to validate my configurations and I am seeing my Excahnge Internal private IP on the recipient headers. This is the only thing that is troubling me but I am open to any suggestions to clean up my configurations at this point.

If I send email via Outlook 2007 through Exchange 2007 to another mail server I get these headers:
Received: from [67.153.yy.xx] (helo=mail.sendingdomain.com)
     by svr002.hostingserver.net with esmtps (TLSv1:RC4-MD5:128)
     (Exim 4.69)
     (envelope-from <useraccount@sendingdomain.com>)
     id 1OVnnd-0000Un-50
     for anotheruser@recipientdomain.com; Mon, 05 Jul 2010 10:41:37 -0500
Received: from svr001.sendingdomain.local ([192.168.2.25]) by
svr001.sendingdomain.local ([192.168.2.25]) with mapi; Mon, 5 Jul 2010
10:35:45 -0500
From: Jim Bob <jimbob@sendingdomain.com>
To: "anotheruser@recipientdomain.com" <anotheruser@recipientdomain.com>
Date: Mon, 5 Jul 2010 10:35:44 -0500
Subject: TESTING ONLY
Thread-Topic: TESTING ONLY
Thread-Index: AcscWJAamQUDiVqFROyUA8wnqoFSTA==
Message-ID: <E2F3FF4C4669C04180DCB53DB71D929C01BC8704E577@svr001.sendingdomain.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/related;
     boundary="_004_E2F3FF4C4669C04180DCB53DB71D929C01BC8704E577svr001G_";
     type="multipart/alternative"
MIME-Version: 1.0

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But if I send an email using an POP3/SMTP connector to Exchange server to send email to the same recipient server, I get the following headers:
Received: from [67.153.yy.xx] (helo=mail.sendingdomain.com)
     by svr002.hostingserver.net with esmtps (TLSv1:RC4-MD5:128)
     (Exim 4.69)
     (envelope-from <TESTING@sendingdomain.com>)
     id 1OVnwz-0000um-SR
     for anotheruser@recipientdomain.com; Mon, 05 Jul 2010 10:51:17 -0500
Received: from PC01 (10.2.2.4) by mail.sendingdomain.com (192.168.2.2) with
Microsoft SMTP Server id 8.1.375.2; Mon, 5 Jul 2010 10:45:26 -0500
From: TEST <testing@sendingdomain.com>
To: <anotheruser@recipientdomain.com>
Subject: TESTING ONLY
Date: Mon, 5 Jul 2010 10:51:23 -0500
Message-ID: <001101cb1c59$ebaea730$c30bf590$@com>
MIME-Version: 1.0
Content-Type: multipart/alternative;
     boundary="----=_NextPart_000_0012_01CB1C30.02D89F30"
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: AcscWetIJuJqU1F7Q+u0YGY3zFg9fw==
Content-Language: en-us

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Both of the above were sent from Outlook. One native to Exchange and the other through a test pop account that was set up. I have no problem sending to any server including the likes of AOL, GMail, AT&T, etc. I am only having an issue sending to the one host system. I can receive from them with no issue whatsoever. This server has been running with no configuration changes for over a year. The recipient server changed their IP address when all of this began. I am resolving the correct IP through DNS. Please, any suggestions are warmly welcomed...

Thanks,
-greg
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Author

Commented:
Sorry, I left out that if I send using Outlook through Exchange native, I get an immediate "Requested #554 Transaction failed ##" back.
Rodney BarnhardtServer Administrator

Commented:
When using a POP3, you would be bypassing your external IP. Do you have an internal spam filter that also filters out going mail either on the client or your network? There could be a blockage there. This message is not an Exchange generated message, it is limited to Outlook. Here are some reason:
554 mailbox limit exceeded - psmtp
554 no relaying allowed - psmtp
554 transaction failed - psmtp

I have even heard of some things like McAfee security causing this problem. Have you checked the logs on your Exchange server? Could it be blocking this client for some reason?
The person on the ISP side of this was a fast talker and caused my own EGO to go into double check mode. So I spent hours combing my own configurations to make certain I was not at fault on this deal. The final issue is that the person who is Hosting this mail server for my client is not as knowledgeable as he would make it seem by his quick speech patterns and handy use of buzz terms that sound important but are unrelated to the issue at hand. My customer on the other hand told him to fix the issue or lose the account... It seems that my email address was mysteriously found in the local server block list and was fixed just a few minutes later. Things that make you go Hmmmmm...