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troubleshooting Question

Exchange 2007 oddity

Avatar of Gregory Miller
Gregory MillerFlag for United States of America asked on
ExchangeEmail ServersEmail Protocols
3 Comments1 Solution1301 ViewsLast Modified:
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 ([]) by
svr001.sendingdomain.local ([]) 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
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
acceptlanguage: en-US
Content-Type: multipart/related;
MIME-Version: 1.0

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 ( by mail.sendingdomain.com ( 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>
Date: Mon, 5 Jul 2010 10:51:23 -0500
Message-ID: <001101cb1c59$ebaea730$c30bf590$@com>
MIME-Version: 1.0
Content-Type: multipart/alternative;
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: AcscWetIJuJqU1F7Q+u0YGY3zFg9fw==
Content-Language: en-us

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...

Avatar of Gregory Miller
Gregory MillerFlag of United States of America imageGeek

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