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here are the headers of the blocked messages (actual domain replaced with domain.com, ip address with n.n.n.n and gmail account name with person.account):

Delivered-To: person.name@gmail.com
Received: by 10.216.89.137 with SMTP id c9cs247685wef;
        Tue, 6 Dec 2011 16:06:37 -0800 (PST)
Received: by 10.224.199.134 with SMTP id es6mr14447757qab.2.1323216395590;
        Tue, 06 Dec 2011 16:06:35 -0800 (PST)
Return-Path: <notifications@domain.com>
Received: from mail.domain.com (domain.com. [n.n.n.n])
        by mx.google.com with ESMTP id b16si7471407qcv.131.2011.12.06.16.06.35;
        Tue, 06 Dec 2011 16:06:35 -0800 (PST)
Received-SPF: pass (google.com: domain of notifications@domain.com designates n.n.n.n as permitted sender) client-ip=n.n.n.n;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of notifications@domain.com designates n.n.n.n as permitted sender) smtp.mail=notifications@domain.com
Received: by mail.domain.com (Postfix, from userid 5001)
  id 26ADE381E3; Tue,  6 Dec 2011 19:06:35 -0500 (EST)
Received: from domain.com (domain.com [127.0.0.1])
  by mail.domain.com (Postfix) with ESMTP id 0148638030
  for <person.name@gmail.com>; Tue,  6 Dec 2011 19:06:31 -0500 (EST)
Date: Tue, 06 Dec 2011 19:06:31 -0500
From: DomainApp <notifications@domain.com>
Reply-To: notifications@domain.com
To: person.name@gmail.com
Message-ID: <4edeae07e069c_7cc1413de46597b2@domain.com>
Subject: Roman Snitko says hi
Mime-Version: 1.0
Content-Type: text/plain;
 charset=UTF-8
Content-Transfer-Encoding: 7bit
X-No-Spam: True
Precedence: bulk
List-Unsubscribe: notifications@domain.com

Messages go to Spam folder on various gmail accounts, so it's not a coincidence.

I followed all gmail guides on sending bulk emails from here https://mail.google.com/support/bin/answer.py?hl=en&answer=81126. I also checked my ip-address here http://www.dnsblcheck.co.uk/ and it's NOT on the blacklists.

Thus I have two questions:

  1. What may be the possible reason for the messages to go to Spam folder?
  2. Is there any way to contact Google and ask them what causes this?

Update: I have set up openDKIM on my server, everything works, gmail message headers say that dkim=pass, which means everything is set up correctly. Messages still end up in Spam folder.

orion3
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    The included headers suggest your email is not signed. One suggestion that seems to make a big difference is to implement DKIM signing. Use OpenDKIM (or DKIMproxy) with Postfix. It does add a bit of overhead, but should improve your delivery rate. – cyberx86 Dec 07 '11 at 00:50
  • This can be based on the content of the e-mail, too. – ceejayoz Sep 11 '13 at 19:00
  • same problem here http://serverfault.com/questions/545189/email-delivery-to-gmail-breaks-after-implementing-domainkey – sazary Oct 12 '13 at 18:21

1 Answers1

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If you follow that google.com support link all the way to the end, there should be a form to contact the postmaster. However, if you just set up the DKIM infrastructure, it may take "a while" for the messages to not be spam:

Were your records incomplete? Yes, my records were incomplete, and I've corrected them

We're glad that you've identified and corrected the problem. Please note that it may take some time for your domain's reputation to be restored, and you may have trouble delivering mail to Gmail users for a short period of time. This problem will resolve itself as you continue to follow the practices outlined in our Bulk Senders Guide.

Aaron
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