Exchange 2003 has issues receiving from external domain.

Posted on 2011-03-10
Last Modified: 2012-08-13

I am having sporadic issues with my Exchange 2003 mail server running on Windows SBS 2003.  Every so often I will get an email from one of our clients that has the domain of, which is based in Israel and I am based in the US, and they state that they received a non delivery report when sending to my domain with error code 4.4.7.  

This is only sporadic, and sometimes I do indeed receive emails from them, and other times not.  I am running Exchange 2003 version 6.5 SP2.  This is really one of the only domains I seem to be experiencing issues when receiving.  I have gone through my local mail queues and cannot find a single instance of the failed message.  It's like it doesn't even hit my Exchange server.  At first I was thinking that this is an issue with their mail server, but I have been made aware that the 4.4.7 errors seem to be related to the "receiving" server and not the "sending" server.  I have checked to make sure my domain is not blacklisted, which it is not, and I also have the correct PTR record set on my domain.  

Any help with this is greatly appreciated as I am at a stand still on what to test and troubleshoot any further.  Thank you.

Question by:rwcm
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LVL 76

Accepted Solution

Alan Hardisty earned 500 total points
ID: 35097550
Well - the sending domain is not RFC compliant and have two MX records, so they could be sending from multiple places too and one server could be configured correctly, and the other not.

Either way - on the surface so far, it looks like they are to blame for their lack of email delivery and they need to sort their end out!

Their 2 MX records are:

100 [TTL=120] IP= [TTL=120] [IL]
10 [TTL=120] IP= [TTL=120] [IL]

Both names point to the same IP Address which is a complete waste of time!!!!

WARNING: One or more of your mailservers is claiming to be a host other than what it really is (the SMTP greeting should be a 3-digit code, followed by a space or a dash, then the host name). If your mailserver sends out E-mail using this domain in its EHLO or HELO, your E-mail might get blocked by anti-spam software. This is also a technical violation of RFC821 4.3 (and RFC2821 4.3.1). Note that the hostname given in the SMTP greeting should have an A record pointing back to the same server. Note that this one test may use a cached DNS record. claims to be host [but that host is at (may be cached), not]. <br /> claims to be host [but that host is at (may be cached), not]. <br />

Plus their SPF record looks wrong and doesn't include their sending server, assuming they send AND receive on the same IP - which they might not!

v=spf1 ip4: ip4: ip4: ip4: ?all"

Author Comment

ID: 35097833
This is very good information and makes complete sense.  Before I contact them to relay information as to what could be wrong on their sending servers end, is there anything else I could try to troubleshoot on my end to test this issue further.  I just want to exhaust all my troubleshooting steps before pointing the blame back at their server.  
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35097848
Do you have any Anti-Spam software installed or a 3rd party filtering your mail before it reaches your server or an Anti-Spam device such as a Barracuda appliance?

Do you use the Intelligent Message Filtering on your server in the absence of any 3rd party / software / appliance?
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 35097853
Put it this way - if they sent my server an email it would be immediately rejected!

Author Comment

ID: 35098002
I use a Red Hat Linux appliance with Symantec Mail Security for SMTP installed for filtering.  I have already tracked and compared my logs with it and my Exchange server and they are identical, so I believe I can safely rule out my Red Hat appliance as a cause wouldn't you say?  
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35100742
Most mail-flow issues lies squarely at the sending server (not all - but most).

Based on their config which I have pointed out - your server is probably just looking at their configuration and rejecting them because they are not configured correctly - and whose fault it that?

Author Comment

ID: 35101284
Thats good to know.  Thanks a lot for your time and knowledge.
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35101288
You are welcome - thanks for the points.


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