Why does gmail flag my server emails as spam?

Question

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:

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;
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=
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?

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. http://support.google.com/a/bin/answer.py?hl=en&answer=178723 — Zoredache, Mar 01 '12 at 23:06

score 1 · Answer 1 · answered Mar 02 '12 at 04:18

1

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.

answered Mar 02 '12 at 04:18

John Gardeniers

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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 02 '12 at 06:58
@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 02 '12 at 08:17

score 0 · Answer 2 · answered Mar 02 '12 at 08:55

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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

answered Mar 02 '12 at 08:55

Lazy Badger

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score 0 · Answer 3 · answered Mar 02 '12 at 15:36

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.

Why does gmail flag my server emails as spam?

3 Answers3