Troubleshooting email delivery for new domains

Posted on 2011-04-20
Medium Priority
Last Modified: 2012-05-11
Problem receiving email on two newly registered domains


Internal Exchange 2003 server sp2

Exchange hosts 6 existing domains for email (5 external) - all working fine
New domain added under Recipient Policies and updated

Internal PineApp unit for filtering email
2 new domains added to accept email delivery

Domainsatcost is registrar and is set to use 3rd party hosting:


Primus (ISP) is doing DNS services and mail relay for both new domains

Copy of NDR from an email sent from an @rogers.com account

Sorry, we were unable to deliver your message to the following address.

Remote host said: 553 sorry, relay denied. [RCPT_TO]

--- Below this line is a copy of the message.

Received: from [] by nm2.access.bullet.mail.mud.yahoo.com with NNFMP; 20 Apr 2011 16:14:41 -0000
Received: from [] by tm9.access.bullet.mail.mud.yahoo.com with NNFMP; 20 Apr 2011 16:14:41 -0000
Received: from [] by omp1014.access.mail.mud.yahoo.com with NNFMP; 20 Apr 2011 16:14:41 -0000

X-Yahoo-Newman-Property: ymail-3
X-Yahoo-Newman-Id: 712430.87933.bm@omp1014.access.mail.mud.yahoo.com

Received: (qmail 91120 invoked by uid 60001); 20 Apr 2011 16:14:40 -0000
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=rogers.com; s=s1024; t=1303316080; bh=ZEIj10JXZWR8DoOqQG4Zl8UUB4ZPNg8nquje8wAAhHI=; h=Message-ID:X-YMail-OSG:Received:X-Mailer:Date:From:Subject:To:MIME-Version:Content-Type; b=ab8d5G0+2NPfTzuvPB4NeZTR+gA/20lZ/cRVPlFT1Cbqzn7fNytLDmjXDuGT17efYXjiwnuGDcyWl/YdCLG9mDqKyon6zA0jZZ4kZeNWPEaFUni62fvNnb1BpQwAQ83em+1ztaJx6apPDPF33PTN+sTgIPg+2hzZNNT/2rnjed0=
DomainKey-Signature:a=rsa-sha1; q=dns; c=nofws;
  s=s1024; d=rogers.com;

Message-ID: <211969.88720.qm@web88208.mail.re2.yahoo.com>
X-YMail-OSG: NXE8wzEVM1mlbGMkaeO8SvyNFR0I.lmpsz8HJPNJblvusUA

Received: from [] by web88208.mail.re2.yahoo.com via HTTP; Wed, 20 Apr 2011 09:14:40 PDT
X-Mailer: YahooMailClassic/12.0.2 YahooMailWebService/
Date: Wed, 20 Apr 2011 09:14:40 -0700 (PDT)
From: ******@rogers.com
Subject: test
To: ******@yegendorflawfirm.ca
MIME-Version: 1.0

If I read the NDR correctly the email is making it to our public IP ( and getting rejected by either our Exchange server or the Pineapp spam unit.  I've gone through both with a fine-toothed comb and can't find any problems, however this stuff is not my forte and I'm probably missing something...

Happy to provide more info.
Question by:DPServices
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LVL 31

Expert Comment

ID: 35434970
Have you tried telneting into your exchange 2003 server on port 25 and sending a mail to one of the new domains?

Have you also ticked the box on the email policy to say 'this exchange server is responsible for delivery to this domain'
LVL 31

Expert Comment

ID: 35435003

Author Comment

ID: 35435323
Hi MegaNuk,

Yes that checkbox is ticked for both domains in Recipient policy.

As for telnet I was able to send a test email...although a few weird telnet errors:

220 DELL.BrazeauSeller.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.395
9 ready at  Wed, 20 Apr 2011 14:07:45 -0400
helo me
250 DELL.BrazeauSeller.local Hello []
mail from:administrator@brazeauseller.com
500 5.3.3 Unrecognized command
mail from:administrator@brazeauseller.com
250 2.1.0 administrator@brazeauseller.com....Sender OK
rcpt to:administrator@yegendorflawfirm.ca
500 5.3.3 Unrecognized command
rcpt to:administrator@yegendorflawfirm.ca
501 5.5.4 Invalid Address
rcpt to:administrator@yegendorflawfirm.ca
500 5.3.3 Unrecognized command
rcpt to:administrator@yegendorflawfirm.ca
501 5.5.4 Invalid Address
rcpt to:administrator@yegendorflawfirm.ca
501 5.5.4 Unrecognized parameter:administrator@yegendorflawfirm.ca
rcpt to:administrator@yegendorflawfirm.ca
250 2.1.5 administrator@yegendorflawfirm.ca
354 Start mail input; end with <CRLF>.<CRLF>


250 2.6.0 <DELLFRaqbC8wSA1XvpF00000004@DELL.BrazeauSeller.local> Queued mail for

The test email was received right away.
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LVL 31

Expert Comment

ID: 35435863
Ok, so it is not exchange then. Try telnet into the pineapp spam unit and perform the same test.

Author Comment

ID: 35436101
I get relay denied errors on the Pineapp unit however I get those errors even for valid domains that the unit currently processes, so I'm not sure if that's a good test or not
LVL 31

Accepted Solution

MegaNuk3 earned 2000 total points
ID: 35436145
Very odd. Maybe you need to telnet into it from an external/Internet connection to see if it accepts those domains. You can do smtp test sends from www.testexchangeconnectivity.com

Maybe it is time to reboot your pineapp box so it reads in the new domains

Author Comment

ID: 35436668
Yeah I'm going to reboot everything tonight.. you're probably right about the telnet thing as well...it's quite restrictive on the internal interface.  I'll update this post tomorrow.


Author Comment

ID: 35441181
So it was a problem with the Pineapp unit...had to contact their support to resolve but it basically came down to the new domains not taking effect on the unit... their support had to remote in and patch the device.. after another reboot mail was flowing properly!!

Thanks for your help Nuk... good to have another set of 'eyes' on the problem as I was slowly going crazy trying to figure this out!!

LVL 31

Expert Comment

ID: 35441208
Glad it is working. Thanks for the points.

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