Emails from webserver going to spam folder

[Rob Hecker2]

I have had an ongoing issue with emails sent from my vps server occasionally being rejected or sent to a spam folder. Hotmail/outlook.com is one of the email systems sending the emails to spam, so I created an outlook.com account to test with.

I have recently taken up this issue again because I just went through David Powers' good tutorial on swiftmailer at lynda.com. Using the swiftmailer class, I have created a new mail process. I have included the email header from the outlook.com email that was sent directly to the spam/junk folder. If anyone can see in it any clue as to why the email was sent to spam, I would appreciate it. First some notes:

• I replaced all the encrypted strings with [goobledygook]
• I replaced my domain names with domainname.net and otherdomain.net. My actual domain names are not on any email blacklist. I also replaced my ip address
• Note that spf = pass and dkim = pass
• The from address is on the same domain as the vps server but the form that processed the email is on a different domain (same server) otherdomain.net

Thanks for any thoughts. Headers follow:

x-store-info:[goobledygook]
Authentication-Results: hotmail.com; spf=pass (sender IP is 01.01.01.01) smtp.mailfrom=rhecker@domainname.net; dkim=pass header.d=domainname.net; x-hmca=pass header.id=rhecker@domainname.net
X-SID-PRA: rhecker@domainname.net
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: [goobledygook]
X-Message-Info: [goobledygook]=
Received: from vps.domainname.net ([01.01.01.01]) by COL004-MC2F47.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23143);
     Sat, 5 Mar 2016 07:01:43 -0800
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed;
    d=domainname.net; s=default; h=Content-Transfer-Encoding:Content-Type:
    MIME-Version:To:Reply-To:From:Subject:Date:Message-ID;
    bh=[four lines of gobbledygook]==;
Received: from vps.domainname.net ([01.01.01.01]:37348 helo=otherdomain.net)
    by vps.domainname.net with esmtpa (Exim 4.86_1)
    (envelope-from <rhecker@domainname.net>)
    id 1acDiA-0000uv-R8
    for domainname@outlook.com; Sat, 05 Mar 2016 07:01:42 -0800
Message-ID: <[gobbledygook]@otherdomain.net>
Date: Sat, 05 Mar 2016 07:01:42 -0800
Subject: Website Message from Roger Right
From:  - No Reply <rhecker@domainname.net>
Reply-To: rob@robhecker.com
To: domainname@outlook.com
MIME-Version: 1.0
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable
X-AntiAbuse: This header was added to track abuse, please include it with any abuse report
X-AntiAbuse: Primary Hostname - vps.domainname.net
X-AntiAbuse: Original Domain - outlook.com
X-AntiAbuse: Originator/Caller UID/GID - [47 12] / [47 12]
X-AntiAbuse: Sender Address Domain - domainname.net
X-Get-Message-Sender-Via: vps.domainname.net: authenticated_id: rhecker/from_h
X-Authenticated-Sender: vps.domainname.net: rhecker@domainname.net
X-Source:
X-Source-Args:
X-Source-Dir:
Return-Path: rhecker@domainname.net
X-OriginalArrivalTime: 05 Mar 2016 15:01:43.0638 (UTC) FILETIME=[EE383F60:01D176EF]

This is the second try. Hope it gets there.

[sinious]

I really do feel for you Rob. I've hit this wall and haven't found that magic formula just yet either. Back in the day it was as simple as if the domain name didn't exactly match the mail leaving, you're in the spam folder. I don't know if "vps" prefixing the server is enough to cause that trip. I doubt it since the suffix matches.

Have you attempted any extremely simple mail with as few headers as possible? Literally a plain text from email, and the subject and body just non-HTML plain text?

[Rob Hecker2]

Have you attempted any extremely simple mail with as few headers as possible? Literally a plain text. . .

Yes, my test was with a plain text email and just the essential headers.

The biggest problem is that before customers can make a purchase they must create an account and there is email verification before they can obtain a password. My clients really don't like it when people complain that they never got the verification email.

[sinious]

Perhaps since it's just a simple text email being generated/sent through the code it's just getting snagged by the standard CAN-SPAM act (lack of an unsubscribe link, etc). That's enough to get an email knocked down alone. More info on that compliance:

CAN-SPAM Act of 2003 - Wikipedia

Are your sender policy framework records up to date since the subdomain contains the sending server? A random explaination:

About SPF records - Google

If you have something like MailChimp installed on your host you might want to try sending from that to see if you get spam-bin'd. If you don't, you can examine the header differences and the email content difference.

Little by little I'm sure you'll find the magic formula for your setup, hang in there!