Why does gmail flag my server emails as spam?

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: [email protected]
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: <[email protected]>
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 [email protected] 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 [email protected] designates 174.143.24.37 as permitted sender) [email protected]; dkim=pass [email protected]
Received: from wordstash.com (localhost [127.0.0.1])
    by wordstash.com (Postfix) with ESMTP id A3E2C134101
    for <[email protected]>; 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: [email protected]
To: [email protected]
Message-Id: <[email protected]>
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?


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.