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MS Exchange 2003 5.3.3 Unrecognized command

Posted on 2010-11-17
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I have a few domains that I am unable to send email to. These were email addresses that I was sending to on a regular basis, until recently when I now get the following bounceback message:

Your message did not reach some or all of the intended recipients.
      Subject:  test
      Sent:     10/28/2010 9:57 AM
The following recipient(s) cannot be reached:
      someone@somewhere.com on 10/28/2010 9:59 AM
            A critical function required for the transfer or delivery of the message was not supported by the originator of the report
            <mail.capitalgazette.com #5.3.3 smtp;500 5.3.3 Unrecognized command>

Following normal SMTP troubleshooting results in the following:
telnet mail.somewhere.com 25
220 **** etc etc...
HELO mail.capitalgazette.com
250 mail.somewhere.com Hello [12.183.22.2]
MAIL FROM me@capitalgazette.com
250 2.1.0 me@capitalgazette.com....Sender OK
RCPT TO:someone@somewhere.com
250 2.1.5 someone@somewhere.com
DATA
500 5.3.3 Unrecognized command.


This happens on all the domains with this particular bounceback, they all fail at the DATA command.
So far I have tried...  adding SPF record, PTR record, correcting the FQDN (it was incorrect previously). Nothing had any affect. I am using Exchange 2003 for outgoing mail, with a Barracuda spam filter set for inbound mail only. One possible common theme is that at least two of the domains I have problems with have "upgraded" to Exchange 2010 (from older versions of Exchange) around the time this started happening.
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Question by:capgaz
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4 Comments
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 34162134
Are you sending mail out via your Barracuda device as well as receiving via it?

If you are, you need to change the FQDN on the device to match mail.capitalgazette.com as it is currently showing the following:
OK: All of your mailservers have their host name in the greeting:

barracuda2.capitalgazette.com

Any receiving servers will see the FQDN and IP address of the connecting server, or in your case, the Barracuda and check the Reverse DNS record of the IP and the FQDN match - in your case they don't because the sending server (Barracuda) is showing barracuda2.capitalgazette.com.

It would also be worth advising of the recipient domains (I can hide all the domain names after resolution or as I go as I am a Zone Advisor and can modify comments).
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Author Comment

by:capgaz
ID: 34165649
I think you hit it, the FQDN not matching the hostname of the reverse lookup. Someone had suggested adding a lower priority MX record for barracuda2, which sounds like it would make sense. I just made that change and am waiting for it to propogate. I'll post back later or tomorrow to see how it goes.
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LVL 76

Accepted Solution

by:
Alan Hardisty earned 2000 total points
ID: 34165844
Adding an mx record should work - just point it to your Barracuda IP and job done.
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Author Closing Comment

by:capgaz
ID: 34205422
Adding the MX record fixed the problem.
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