SMTP server

My SMTP server does not deliver messages to a certain domain. It is able to send to others. What could be the problem? The message shows up in the "bad mail" folder below:

Date: Thu, 31 Mar 2011 11:08:38 -0500
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
X-DSNContext: 7ce717b1 - 1142 - 00000001 - 00000000
Message-ID: <>
Subject: Delivery Status Notification (Failure)

This is a MIME-formatted message.  
Portions of this message may be unreadable without a MIME-capable mail program.
Content-Type: text/plain; charset=unicode-1-1-utf-7

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.
Content-Type: message/delivery-status

Reporting-MTA: dns;
Received-From-MTA: dns;server
Arrival-Date: Thu, 31 Mar 2011 10:20:59 -0500

Final-Recipient: rfc822;
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550 #5.1.0 Address rejected
Content-Type: message/rfc822

Received: from iedaww004 ([]) by with Microsoft SMTPSVC(6.0.3790.4675);
       Thu, 31 Mar 2011 10:20:59 -0500
thread-index: Acvvtz1OongXvN0bQIqcEBqP7qEfwQ==
Thread-Topic: Attendance Notification

Content-Type: text/plain;
Content-Transfer-Encoding: 7bit

This is to notify you that Associate - Luz name in Eligibility
Support Spanish city) has called in FMLA as of 3/31/2011 5:45.

Other Comments: FMLA


Thomas NSystems Analyst - Windows System AdministratorAsked:
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Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
It seems very flaky as well when it sends to other domains. Sometimes I would get 5 out 15 messages.
Could be a problem with spam filters.  Check to make sure your IP or domain are not in a black hole list
Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
What is a black hole list?Thanks
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Here is the error code for the problem your having
 Final-Recipient: rfc822;
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550 #5.1.0 Address rejected

THis would most likely be an issue on the reciepients server not yours

To troubleshoot you will want to telnet and test - use nslookup to check dns
Here is a link with troubleshooting using telnet

Go thru the telnet steps in the article and you should get a better idea of what the problem is.

This link has all the diag codes - including yours

Numeric Code: 5.1.0

Possible Cause: This code indicates a general categorizer-based failure (bad address failure). An e-mail address or other attribute could not be found in the directory. This issue may occur if contact entries do not have the targetAddress attribute set. This issue occurs most frequently when MDAccess receives "object not found" errors from DSAccess when the Categorizer is doing the homeMDB lookup on a user.

This issue also occurs if you used Microsoft Outlook to save your e-mail message as a file and someone opens and replies to this message offline. The message property only preserves the legacyExchangeDN when Outlook delivers the message. Therefore, the homeMDB lookup may fail.

Troubleshooting: Verify the recipient address and resend the message. Verify that the recipient address is formatted correctly and that the categorizer was able to correctly resolve the recipient.
Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
thanks Pudgley. Have you ever run the smtpdiag before? I downloaded and tried to run the .exe and it just flashes and goes away. Is there a GUI thats suppose to open up? Thanks
A black hole list is servers that have been identified as spam servers and some SMTP servers are configured to drop all connection from those servers.

Make sure you are using the person's actual email address and not just a forward.  Sometimes that can cause issues.
Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
I tried to telnet and run the commands but this is what it gives me. Invalid address when I try to use the "rcpt to:" part. I tried different addresses with no luck. Has anyone else run into this?

ehlo Hello []
250-SIZE 20480000
250 OK

250 2.1.0 OK
rcpt to: any email address
501 5.5.4 Invalid Address
Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
I added an email address of someone on there domain and I get error"500 5.3.3 unrecognized command"
just a quick question/assumption
you can mail this person from like gmail or hotmail right?

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Thomas NSystems Analyst - Windows System AdministratorAuthor Commented:
I found the answer, the receiving domain is filtering my domain as spam we believe. I will award points though to the person who spent the most time helping me.
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