Email always goes to spam and not inbox on GMail

Question

No matter what I do, email will not go to my inbox. This is the header:

Delivered-To: jcink2k@gmail.com
Received: by 10.60.63.109 with SMTP id f13csp15507oes;
        Sat, 30 Nov 2013 06:51:41 -0800 (PST)
X-Received: by 10.68.194.71 with SMTP id hu7mr21598493pbc.68.1385823101241;
        Sat, 30 Nov 2013 06:51:41 -0800 (PST)
Return-Path: <apache@s2.jcink.com>
Received: from s2.jcink.com ([199.59.166.170])
        by mx.google.com with ESMTP id it5si42774013pbc.155.2013.11.30.06.51.40
        for <jcink2k@gmail.com>;
        Sat, 30 Nov 2013 06:51:41 -0800 (PST)
Received-SPF: pass (google.com: domain of apache@s2.jcink.com designates 199.59.166.170 as permitted sender) client-ip=199.59.166.170;
Authentication-Results: mx.google.com;
       spf=pass (google.com: domain of apache@s2.jcink.com designates 199.59.166.170 as permitted sender) smtp.mail=apache@s2.jcink.com
To: jcink2k@gmail.com
Subject: Hey everyone
X-PHP-Originating-Script: 0:index.php
From: admin@s2.jcink.com
Reply-To: jcink@s2.jcink.com
Message-Id: <20131130145140.891B31542AB@s2.jcink.com>
Date: Sat, 30 Nov 2013 06:51:40 -0800 (PST)

This is a quick email just to see what happens.

What could be wrong here? I have a ptr record set up for the IP address as well as an SPF record. It even says SPF=Pass. This doesn't make sense.

Answer 1

Maybe the X-PHP-Originating-Script makes gmail think that it is possibly spam. You are using a domain with a subdomain, moreover the name is ending in a number. s2.jcink.com does not have an MX record. jcink.com does have an MX record, but points to ASPMX.L.GOOGLE.com. Is that a real MX server you are authorized to use? I am just guessing. Most likely the IP address you use is new. You have to wait and if there are no spam from the IP address, it will get better reputation, and gmail will put the mails into the normal folder.

I also experienced strange things with gmail. Users reported several times that mails sent to their gmail account is missing, it is not even in the spam folder. I checked the logs and gmail accepted the mails in these cases. Accepting the mail means that - according to rules defined by the SMTP RFC - gmail is responsible for the mail. It either has to deliver to the user, or send back a bounce message to the sender. It must not lose the mail. I could not check the user's gmail account, so maybe they had some settings or something, or they somehow had not noticed the mail, even if they checked.

Answer 2

Something is wrong with your DNS. From the headers that you posted, It looks like your MTA's IP address is 199.59.166.170. If I do a reverse DNS lookup on 199.59.166.170, the PTR record points to s2.jcink.com. However, a DNS lookup of s2.jcink.com resolves to 199.59.166.212 (which is different than the above IP address). This is probably the problem.

Whatever hostname your MTA identifies itself as (in this case s2.jcink.com) should resolve to the IP address that your MTA is connecting from, and this IP should have a PTR record that points to this same hostname. If not, most spam filters will likely flag messages from your MTA as spam.