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Spam filtering issues!

Posted on 2011-03-09
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Last Modified: 2012-05-11
I have a client who is sending mail to lots of clients through a group called Boberdoo, who also uses another company SendGrid to actually send the emails through.

The domain we're sending from is mercuryroadassociates.com. The messages that are being sent are fairly simple, some information about a client, their email address, website link if applicable, and a link back to the Boberdoo lead distribution site.

GoDaddy and Google Apps (standard, not the sweet Postini filtering version) accept the mail with no issue, however I have to completely disable the spam filter on Comcast to let them through, and my own Exchange server with McAfee hosted spam filtering gives it a 99.9999% spam confidence rating and defers it right away.

The SendGrid company appears to do everything correctly as they're signing messages with DKIM and also have valid SPF records.

Where should I begin?

Attached is a long header for the message that made it into my inbox.
From: 	info@mercuryroadassociates.com
	Subject: 	Mercury Road Associates Leads Delivery (Executive/Entrepreneur Call Verified Lead)
	Date: 	March 9, 2011 4:09:12 PM MST
	To: 	Jordan  Philip <jordan@thewiredconnection.com>
	Reply-To: 	info@mercuryroadassociates.com
	Delivered-To: 	jordan@thewiredconnection.com
	Received: 	by 10.14.126.10 with SMTP id a10cs88086eei; Wed, 9 Mar 2011 15:09:15 -0800 (PST)
	Received: 	by 10.236.27.98 with SMTP id d62mr29203yha.5.1299712154766; Wed, 09 Mar 2011 15:09:14 -0800 (PST)
	Received: 	from o208115235243.static.reverse.sendgrid.net (o208115235243.static.reverse.sendgrid.net [208.115.235.243]) by mx.google.com with SMTP id j44si5815576yhn.206.2011.03.09.15.09.12; Wed, 09 Mar 2011 15:09:13 -0800 (PST)
	Received: 	by 10.12.16.30 with SMTP id mf25.651.4D7808988 Wed, 09 Mar 2011 17:09:12 -0600 (CST)
	Received: 	from leads.mercuryroadassociates.com (unknown [10.9.180.5]) by mi8 (SG) with ESMTP id 4d780898.68e7.2d78a3 for <jordan@thewiredconnection.com>; Wed, 09 Mar 2011 17:09:12 -0600 (CST)
	Return-Path: 	<bounces+22173-5f95-jordan=thewiredconnection.com@sendgrid.me>
	Return-Path: 	info@mercuryroadassociates.com
	Return-Path: 	info@mercuryroadassociates.com
	Received-Spf: 	pass (google.com: domain of bounces+22173-5f95-jordan=thewiredconnection.com@sendgrid.me designates 208.115.235.243 as permitted sender) client-ip=208.115.235.243;
	Authentication-Results: 	mx.google.com; spf=pass (google.com: domain of bounces+22173-5f95-jordan=thewiredconnection.com@sendgrid.me designates 208.115.235.243 as permitted sender) smtp.mail=bounces+22173-5f95-jordan=thewiredconnection.com@sendgrid.me; dkim=pass header.i=@sendgrid.me
	Dkim-Signature: 	v=1; a=rsa-sha1; c=relaxed; d=sendgrid.me; h=date:to :from:reply-to:subject:message-id:mime-version :content-transfer-encoding:content-type:sender; s=smtpapi; bh=JI EVzTnb+rxIEa7ij54YlBMhtZ0=; b=Pl8aj0nUkm7H16EOrAkQ5SttVCex+nxLxQ S57dJX/2SfN++cs5CNvoCz297Cww+MSj9aszAA3HFuxDGml+h28bmsWbRNoQYIS3 SpdV84N/hbJ3NnzwUZrinZj7zhMkmYCWXGx7FU8GWxEJW1EnMQ4v+kimcOS/efgf fH3QQ6r6I=
	Domainkey-Signature: 	a=rsa-sha1; c=nofws; d=sendgrid.me; h=date:to:from :reply-to:subject:message-id:mime-version :content-transfer-encoding:content-type:sender; q=dns; s=smtpapi; b= iX8J8Z92DNE4iZHxwj1NGp+sm/t5YYMAf/BEvj727LKkNkwQEEq5yPqLpDkR/YBe yu+31b9jB2FE89isXkmjnsu2Z99IGKikTE4iQN26X6G3OyLIWBnKzwSDZAfYLCs9 Vlw+kx9uRhKUo5jOnxWU2N3Vs+OjNJzKCjzuUaRgsbQ=
	Message-Id: 	<d85c6aac0294fbaa100535c9f92f66e5@leads.mercuryroadassociates.com>
	X-Priority: 	3
	X-Mailer: 	PHPMailer [version 1.72]
	Error-To: 	support@boberdoo.com
	Customid: 	fb73734788e54d052f3eb2fb559263
	Mime-Version: 	1.0
	Content-Transfer-Encoding: 	quoted-printable
	Content-Type: 	text/html; charset="utf-8"
	X-Sendgrid-Eid: 	kVrI9L/yb7s7F+cx3JaGNjcop0EZLT2/qPH8dp4asPggJAt+4EwA0NU6QLSUf8TIs/P+NkSANXNlY5MIVGuBb2fRfC0CluPSTK1lZSeh3i01SLJLfRiEgG9Iel3By3pHcWyoGLMrUPY2PWF8OGzGlZwQAv6Kt43ra01t/B9rFvM=
	Sender: 	Info@Mercuryroadassociates.Com <info=mercuryroadassociates.com@sendgrid.me>

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Question by:newtoexchange
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Expert Comment

by:Alan Hardisty
ID: 35089182
leads.mercuryroadassociates.com resolves to IP 204.93.131.29

Telnetting to that IP shows a server header of da1.boberdoo.com

Running nslookup on da1.boberdoo.com returns an IP address of 204.93.131.60

Reverse DNS for da1.boberdoo.com is da1.boberdoo.com so the problem seems to be that when mail is sent from IP 204.93.131.29 - the FQDN of da1.boberdoo.com resolves back in DNS to a different IP Address and as such, some anti-spam software will reject the messages.
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Author Comment

by:newtoexchange
ID: 35097858
Forgive me as I'm semi-confused about the header.

Ok, so the problem seems to be with the leads.mercuryroadassociates.com, which is sending the email over to sendgrid, which is then sending it out to the client? Would that be correct?

Is sendgrid just relaying the mail?


 
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 35097938
Yes - mercuryroadassociates.com send mail to sendgrid which then send it out to the world.

The configuration of the mercuryroadassociates.com is not RFC compliant by the looks of things, so may get rejected by some servers as the IP for leads.mercuryroadassociates.com ends .29 yet the FQDN of the server that responds on that IP resolves back to a different IP Address.
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Author Comment

by:newtoexchange
ID: 35098027
Ok, this makes sense, so basically changing to another email relay company will not change the outcome since the originating server isn't configured properly, and this is where the issue is coming from.

Since I don't have access to these boberdoo servers, is there something that I could send to them so they could easily fix it?

Could they just change the FQDN of the server that responds on that IP so that it resolves properly to the correct IP address?
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LVL 76

Accepted Solution

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Alan Hardisty earned 500 total points
ID: 35100725
Send them a link to my article!

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/A_2427-Problems-sending-mail-to-one-or-more-external-domains.html

Ask them to check their own server and make sure they comply with RFC standards and if they are still confused - ask them to email me at alan @ it-eye.co.uk and read the rejection message carefully and fully!
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