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I recently moved my server to a new slice at slicehost and since, gmail has been flagging my email as spam. I have added domain keys, created a SPF record, have reverse dns setup, and my ip is not blacklisted. This is a header from a server email:

Delivered-To: address@gmail.com
Received: by 10.204.190.208 with SMTP id dj16csp73539bkb;
        Thu, 1 Mar 2012 14:16:43 -0800 (PST)
Received: by 10.236.170.193 with SMTP id p41mr7956047yhl.15.1330640203327;
        Thu, 01 Mar 2012 14:16:43 -0800 (PST)
Return-Path: <no-reply@wordstash.com>
Received: from wordstash.com (wordstash.com. [174.143.24.37])
        by mx.google.com with ESMTP id i19si1775474anm.152.2012.03.01.14.16.42;
        Thu, 01 Mar 2012 14:16:43 -0800 (PST)
Received-SPF: pass (google.com: domain of no-reply@wordstash.com designates 174.143.24.37 as permitted sender) client-ip=174.143.24.37;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of no-reply@wordstash.com designates 174.143.24.37 as permitted sender) smtp.mail=no-reply@wordstash.com; dkim=pass header.i=@wordstash.com
Received: from wordstash.com (localhost [127.0.0.1])
    by wordstash.com (Postfix) with ESMTP id A3E2C134101
    for <address@gmail.com>; Thu,  1 Mar 2012 22:16:42 +0000 (UTC)
DomainKey-Signature: a=rsa-sha1; s=2007; d=wordstash.com; c=simple; q=dns;
    b=FyJCn+2G3kkoog1hFirsGshOVBXkt9nRqeYdn8JlsYfv/kNPHPO6aP8IYY+eMW235
    w+fUHpk+PY6zUxFCXRb+ZIgXblldE9FZcKEahx8MBvMVoKpn7mXwt9UTWkQCdo1NHpf
    YgvITsbdA+VTgZQp5EJwW/Wy9wh/bggmmpz28bQ=
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=wordstash.com; s=mail;
    t=1330640202; bh=HkYCcviucPKdMQ0B0WPGE0xQP4i8bbutSZj1ExZe/Zc=;
    h=Date:From:To:Message-Id:Subject:Mime-Version:Content-Type; b=bBBv
    fjBBPp/iMKHtuFdjBal4kFtJyBz1O0t0VcrFV9lcGr2Fia9d7MLkNlPRICx5vw2eJgi
    ksIzWvpPWoXtF76003oMpYJKbpLJAAqRVUAMS4MMVbG+necvgFIlcsxjHdNYT7jyYMR
    gSeYSVLtOBJ4m7885Wa6qwdW/+clBXo68=
Date: Thu, 1 Mar 2012 22:16:42 +0000
From: no-reply@wordstash.com
To: address@gmail.com
Message-Id: <4f4ff54a9f00b_38d13fb33f42f16c184d@wordstash.com.tmail>
Subject: Flashcard List: GRE Vocabulary
Mime-Version: 1.0
Content-Type: text/plain; charset=utf-8

Everything seems to be in order. Anyone have any suggestions? I am at a loss. I am using postfix.

Update: I was just thinking, I have a feedback form and I send this form as an email using the user's email as the from email, so I do send some emails that say they do not come from my server. Maybe this triggered the spam filter by google? If so, is there any way to overcome this?

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3  
Your SPF record seems a bit unusual. Why didn't you just do "v=spf1 ip4:174.143.24.37 include:_spf.google.com ~all instead of what you currently have ("v=spf1 ip4:174.143.24.37 mx:alt1.aspmx.l.google.com mx:alt2.aspmx.l.google.com mx:aspmx.l.google.com mx:aspmx2.googlemail.com mx:aspmx3.googlemail.com mx:aspmx4.googlemail.com mx:aspmx5.googlemail.com -all")? That is what is suggested by Google. support.google.com/a/bin/answer.py?hl=en&answer=178723 –  Zoredache Mar 1 '12 at 23:06
    
Ok, thanks, I will change that. –  TenJack Mar 2 '12 at 3:58

3 Answers 3

The sender's address should not be the recipient's address. Having that will appear as if your system is sending on behalf of the recipient's domain. As it's highly unlikely the recipient's SPF record will include your system, at the very least this will increase your spam score. As you have already guessed, the sender should be your system, or at least an address in your domain.

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I've maybe had 20 total emails sent like this. Do you think this enough to damage my spam score? Is this something that changes over time? –  TenJack Mar 2 '12 at 6:58
    
@TenJack, the spam score I was referring to is the one used on a per message basis to determine if that particular message is spam. Whether or not 20 of those will affect your domain's rating is hard to know. –  John Gardeniers Mar 2 '12 at 8:17

Remember one thing: technically correct bullshit is bullshit anyway

Content-analyzer (which works on Google mail) may find a lot of signs of spaminess, except already visible:

  • spammy Message-ID
  • shitty Subject
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Senderscore think that your IP's reputation has recently improved quite dramatically. Since IP reputations tend to have quite a bit of inertia, it's likely that Google still remember their own record of that IP's bad reputation. As long as you aren't sending any spam currently, the reputation should improve slowly until your email ends up back in inboxes again.

If your Gmail recipients are marking your emails as spam then your reputation will not improve, no matter how long you wait.

A List-Unsubscribe: header can help dramatically with improving your reputation. I have read (but haven't yet verified) that Google will use this header to automatically unsubscribe anyone who clicks the spam button in Gmail. This allows you to avoid sending mail to people who don't want it, which is better for everyone concerned.

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