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Unable to send e-mail to one specific domain

Posted on 2006-11-27
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Last Modified: 2008-02-01
I've looked all over EE for the answer to this one with no luck.  We are not able to send e-mail to one specific domain which I will call domain.com.  When sending an e-mail, an Undeliverable message comes back immediately:

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

      Subject:      Test Message from United Seminary
      Sent:      11/27/2006 9:29 AM

The following recipient(s) could not be reached:

      person@domain.com on 11/27/2006 9:29 AM
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <mail.unitedseminary.edu #5.5.0 smtp;550 - Requested action not taken: relaying denied>

This message is immediate and generated by our Exchange server.  People from this domain are able to send e-mail into us.  I've checked and neither of us are blacklisted.

Any ideas?
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Question by:lenkne
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Accepted Solution

by:
dskillin earned 2000 total points
ID: 18021439
Take a look at http://senderbase.org and http://www.trustedsource.org , in the search field enter your IP, view the results, then enter your domain name and review the results.  This may shed some light on the problem.

Also, ensure that you have correct MX, PTR, and A records in DNS for your mail server.

Visit this website from your mail server.

http://www.ipchicken.com/

This will verify the IP and hostname that others see you as.  If this is different from your PTR and MX records, you should update your DNS information.

Investigate putting an SPF record in your DNS for your mail host.  Information, and a wizard to create the record is at:

http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/

Another troubleshooting step would be to send mail to

 check-auth@verifier.port25.com

Review the results and look for failures (everything should pass).

If any of the above fail, you have some cleanup to do, usually with DNS.

Look in your eventvwr, see if any logs are there for the connection at 9:29, this may provide information as well.  You'll find the failed event in your Application log.

Another step you can do is a manual SMTP connection with the telnet command.

http://www.yuki-onna.co.uk/email/smtp.html

This will often produce messages that you can use for further analysis.

Also, if all else fails, you can contact the IT staff at the recieving organization and discuss the problem with them.  It's possible they have you blacklisted for another reason.

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LVL 1

Assisted Solution

by:dskillin
dskillin earned 2000 total points
ID: 18021501
As an aside, your MX hosts presently have a reputation of "suspicious" on trustedsource.  They are showing huge gains in mail activity in the past month as well per senderbase.

Your hosts were listed as:

smtpin7.usinternet.com
smtp1.mke.securence.com

It's quite likely that you're getting bounced by the recieving ends spam software/hardware.
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LVL 104

Expert Comment

by:Sembee
ID: 18021548
If it is a single domain, have you called them up to find out why they are bouncing your messages? Actually asking them might be quicker and will allow you to find the solution.

Simon.
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LVL 14

Expert Comment

by:Ehab Salem
ID: 18025786
Fully agree with Sembee. contacting the recipient admin is the first step. Ask them also which RBL they are using.
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Author Comment

by:lenkne
ID: 18028009
Both responses got us pointed to the source of the problem.  It was a DNS issue with our ISP because the receiving domain had hosted their e-mail with the same ISP as us, but recently moved to another.  Our ISP had not cleaned up their DNS.  Using the tools Sembee suggested and dskillin pointing out the MX record in the log was our ISP, not ours put it all in place.    

Thanks!
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