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What is blocking my outgoing email

Posted on 2009-04-10
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Last Modified: 2012-05-06
Email  to a few specific domains is  being marked as spam by my own server (Exchange 2007 on Windows 2003).  I have disabled all of Exchange's anti-spam and I still get the error. Here is an example header from the NDR:

---------------------------------------------------------------------------------------------------
Delivery has failed to these recipients or distribution lists:

JohnDoe@subdomain.domain.com
An error occurred while trying to deliver this message to this recipient e-mail address.    Microsoft Exchange will not try to redeliver this message for you. Please try resending this message, or provide the following diagnostic text to your system administrator.

The following organization rejected your message: ESMTP.

  _____  

Sent by Microsoft Exchange Server 2007


Diagnostic information for administrators:

Generating server: Domain-Server.abm1.local

JohnDoe@subdomain.domain.com
ESMTP #554 Transaction Failed Spam Message not queued. ##

Original message headers:

Received: from Domain-Server.abm1.local ([172.16.1.2]) by
 Domain-Server.abm1.local ([172.16.1.2]) with mapi; Fri, 10 Apr 2009 13:50:20
 -0700
From: My Name <MyEmail@abm1.com>
To: "JohnDoe@subdomain.domain.com" <JohnDoe@subdomain.domain.com>
Date: Fri, 10 Apr 2009 13:50:19 -0700
Subject: test
Thread-Topic: test
Thread-Index: Acm6HfWc9SAYN9kFTYGkVssNklYI2Q==
Message-ID: <A44508DEF0A01246BA03D5332B13EBF265AF204260@Domain-Server.abm1.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/alternative;
      boundary="_000_A44508DEF0A01246BA03D5332B13EBF265AF204260DomainServera_"
MIME-Version: 1.0

---------------------------------------------------------------------------------------



What are some possible causes of this error?  It just started a few days ago.  The only thing that changed is a certificate expired and was replaced about a month ago.  If you would like to see certain logs, I can post them.
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Question by:BEKtech
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Expert Comment

by:Mestha
ID: 24119765
It isn't your server that is blocking the messages.
All that is happening is the remote server is rejecting your message at the point of delivery and forcing your server to generate the NDR. That is actually the best way to deal with spam messages.

As for why, hard to say. The remote site thinks your server is a source of spam.

Check your send connector is configured correctly - it should be your external FQDN, so mail.example.com not server.example.local
Valid reverse DNS entry and that you are not on any blacklists would also be something to check.

Simon.
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Author Comment

by:BEKtech
ID: 24119812
Isn't this my server? "The following organization rejected your message: ESMTP"  This is the first time I have ever seen this, so I could very well be wrong, but I have seen it list the server that actually rejects listed.  For example, "The following organization rejected your message: mail.someplace.com."
 Just making sure I understand all of this  :)
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Accepted Solution

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Mestha earned 500 total points
ID: 24119948
No, that is not your server rejecting the message.

That is actually poor SMTP headers on the remote server.
Furthermore the message you have posted is not an Exchange message. Exchange doesn't say things like that. I think that is a Postfix error, but I might be wrong there.

Simon.
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Author Comment

by:BEKtech
ID: 24139834
Thank you for your help.  After many hours of checking blacklist, reconfiguring servers, changing MX records...it was my McAfee Trusted Source Rating.  I petitioned them, they upgraded my status, and email is flowing once again.  Thank you!
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