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550 5.7.1 Message rejected due to content restrictions

Posted on 2007-11-17
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One of our customers has an Exchange 2003 server running on Windows 2000 SP4 (server).  They had a major failure yesterday (active directory restore, exchange database repair).  I have sent several test messages through their server to various domains without any problems.  However, when I send email to my own email address (outside domain) I get the following message:

Your message did not reach some or all of the intended recipients.

Subject: test22
Sent: 11/17/2007 8:51 AM

The following recipient(s) could not be reached:

  kip@fresnonetworks.com on 11/17/2007 8:52 AM
  You do not have permission to send to this recipient. For assistance, contact your system administrator.
  <ctfa02.intranet.caltreefruit.com #5.7.1 smtp;550 5.7.1 Message rejected due to content restrictions>

I have checked the content restrictions on the SMTP connector and cannot find anything.  I have also deleted the connector and recreated it.

The receiving server is Exchange 2007 (far-end).  It has multiple SPAM options setup.  I had figured that it (far-end)was blocking the test message but the error comes from ctfa02.intranet.caltreefruit.com which is the SMTP (exchange 2003) server sending the test message.

Again, at this point I think this is only happening when we send to this single domain.  Other test messages to other domains have gone through OK.

Also, one more crazy thing, if I send a message from the receiving (far-end) domain, it goes through fine.  Then, if I forward that same message back to the original sender at the far-end domain, it goes through.  So, the only thing that is being blocked is new messages sent from the Exchange 2003 server to the outside domain (fresnonetworks.com).

Any helps would be appreciated!
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Question by:kharoldsen
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Sembee earned 2000 total points
ID: 20305843
The fact that your server is on the error message doesn't mean it was rejected by your server. What it means is that the remote server rejected the message at point of delivery and forced your machine to generate the NDR. That is the best way to deal with spam.

Have you confirmed the new server is configured int he same way? Presuming that this worked before, DNS will not be an issue, but have you over looked anything? SMTP banner for example? Perhaps the server wasn't sending email directly, but via a smart host at the ISP.

Simon.
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Author Closing Comment

by:kharoldsen
ID: 31409733
Turns out that our spam filter in Exchange 2007 was blocking their IP.  Thanks for the info on the NDR.  I assumed since the NDR was showing as from the internal server that our remote server was not causing the problem.
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