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unrouteable address from Exchange 2003

Posted on 2011-02-22
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Last Modified: 2012-05-11
I have an Exchange server 2003 with sp2.  I have one domain that I am trying to send an email too that I get a bounce back from my server of message 550 unrouteable address.  I can receive emails from this person and have checked with my web hosting company that we relay our out going emails through to make sure we are not blacklisted.  The provider can send mail to this domain in question and can receive as well.  I have had the owner of the other domain check with their provider to make sure that nothing is getting blocked and to make sure the provider he is using does not have a problem with us relaying email through our web hosting company.  There was nothing that came up on their end.  The fact that I am getting this bounce back from my Exchange server lets me know that it is not even leaving my network.  I am not having any problems sending mail to any other domains and receiving mail is working fine.  I have been told that it may be in my DNS of the exchange server.  That is may be holding an old DNS entry for the domain.  Any help on this matter would be greatly appreciated.  Thank you in advance.
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Question by:tdogizhere
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11 Comments
 
LVL 3

Expert Comment

by:Freaky_Friday
ID: 34957219
Hello tdogizhere,

Perhaps you read this KB article already, but if not please review this first: http://support.microsoft.com/kb/300171

This TechNet article also walks you through the steps to check the DNS MX record for the domain your'e trying to reach: http://technet.microsoft.com/en-us/library/aa998082(EXCHG.65).aspx

Next thing you need to do is log in to the Exchange server and manually send an email to the domain you're having problems reaching. Refer to this Microsoft KB article for detailed instructions:
http://support.microsoft.com/kb/153119

Hope this helps!

-Friday

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LVL 16

Expert Comment

by:Postmaster
ID: 34957313
Check if you have a CONTACT entry in your GAL for this address. If so, it may be that the address resolves locally rather than going out to your relay.
I suggest that any non-hosted domain address is removed from your GAL.
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LVL 1

Author Comment

by:tdogizhere
ID: 34957626
It appears that when I do a nslookup and check the MX record for the address I am looking for it resolves to a different IP address and FQN.  Is there a way to flush that out and let it pull new information?  That is part of my DNS server isnt it?
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Author Comment

by:tdogizhere
ID: 34957784
Postmaster, what are you referring to when you say GAL?  
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LVL 1

Author Comment

by:tdogizhere
ID: 34957806
Postmaster, I figured out what you meant and no there is not an entry in there for them.  We have never even communicated with this domain until about a month ago.  And we get their emails but can not get our emails to go to them.  I believe it is going to have something to do with the MX record and think it is going to be on my system.  I really hate inherited problems.
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LVL 16

Expert Comment

by:Postmaster
ID: 34957831
yes - they can be a challenge. MX records will show up via NSLOOKUP's, and should lead you to the source of that record. It is then a matter of getting the record removed. As a fast fix, you can always add a static route for that domain to the same IP that is shown in the public address - but only as a last resort, and always well documented.
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 34958832
Check your hosts and lmhosts.sam files in c:\windows\system32\drivers\etc

Sometimes people add specific IP's and host names in these files and that can cause problems.
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LVL 1

Author Comment

by:tdogizhere
ID: 34960452
After looking at the MX records again I find that they are pointing to the correct servers.  I had been given the wrong address at first but found that the records are pointing to the correct inbound server.  I have followed through with the SMTP test of connecting through relay and have found that I was able to connect to that smtp server and send a test message.  I am still however unable to send from my outlook program to through my exchange server to this domain.  I have noticed that I only get one bounce back from one user.  The other user I send mail too does not get it and I do not receive any error that it did not go through.  I have also checked my LMhost and host files and there is nothing that stands out there either.
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LVL 1

Author Comment

by:tdogizhere
ID: 34960637
I would like to point out that we are pointing all of outgoing mail to a mail relay and that this particular domain I am trying to send to does not even get that far.  The NDR comes from my server.
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LVL 1

Accepted Solution

by:
tdogizhere earned 2000 total points
ID: 34962508
OK.  I was able to figure it out.  I went into my SMTP logging and checked off all the extended options and read through the log file and found out that my Exchange server was trying to send the email out to the other domain but was getting a rejection from the SMTP relay before the message was handed off.  The reason for this was the SMTP server was once the same server the domain was on that I was trying to reach.  When they left that company someone did not remove the domain from the server like they were supposed too and my mail was not making it to the right server on the internet.  I was able to see all of that in the log file and contacted my smtp relay tech support and sent them over the log files and showed them that it was them.  Up to that point they said it was on my system because they did not see anything in their logs that I was sending the message.  They said they were sorry and pulled the information off of their system and all is working fine now.  So thank you all for your help.
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LVL 3

Expert Comment

by:Freaky_Friday
ID: 34974849
If he hadn't reviewed the documentation provided by the Expert commenters, he would not have been able to look in the correct places to determine the issue.
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