Amazon SES and Hotmail spam - google-apps

I configured an email address with google apps for my company. When I send messages from Gmail to address#hotmail.com the message is received correctly in the inbox folder.
When I moved to Amazon SES, I configured correctly SPF and DKIM so that it may work fine. The big problem is that when I send from SES emails go allways into the spam folder!!!
This is the hotmail header of a message that is falled into the spam folder:
x-store-info:CnuewmGKkJzNjuOw4Ko28wB3rXpWYbsxTq8bIGVpexou/aH5YlneZSXtbrTNbKJ4GoT+OaKU2vnoHLIPY7tpJ7yfD4ei7NGnJPMqwC1IOiYDYaHi7z9UqM7HFUFg9PvdD/GTLm1Joes=
Authentication-Results: hotmail.com; spf=pass (sender IP is 54.240.8.95) smtp.mailfrom=0000014191bce21d-5857cbb3-7185-4a04-a62d-02029457d42b-000000#amazonses.com; dkim=pass header.d=beaudience.com; x-hmca=pass header.id=support#beaudience.com
X-SID-PRA: support#beaudience.com
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTE7YT0xO0Q9MjtHRD0xO1NDTD00
X-Message-Info: 11chDOWqoTmYiARgB8x0CqssYC30R1hAxykCxY7lMqvPXk+fm44PmUeqp2eso9uKqBo8WFDhDk3rZsgJn8uSIHpUqpn7/N+/COouobxjVl2F7FiiDMh/AjlIDYLoKhZeWqATlTzu9cdwruznM5Eh3gOw+h4szTV5OcHunEoeFZeggqKm4r8Wd97fzBr3wpj6Xji14R+Xo8C7zTF5xkQAV15Ns/IGAE0R
Received: from a8-95.smtp-out.amazonses.com ([54.240.8.95]) by COL0-MC3-F51.Col0.hotmail.com with Microsoft SMTPSVC(6.0.3790.4900);
Mon, 7 Oct 2013 00:06:18 -0700
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/simple;
s=fzsj4xlkgrzw4njd7a4n5dv47w5dmrc5; d=beaudience.com; t=1381129577;
h=Date:To:From:Reply-To:Subject:Message-ID:MIME-Version:Content-Type:Content-Transfer-Encoding;
bh=d9cLexwYe6DbP7/N2SXpl7aOUi58tQ37WMdTDDTQtvA=;
b=rR0at2KyIFuhpI6HFSd56LbiVPS2uPzECnYlscb7UliQraxznWxjRKrDCF3HVNJj
1/s3xjXaOLoCLk0H0B8xa76KzWgMwtxDulEFn39G06yRd9/r/17xTYzQ/MpMMn9lUlv
VT75xxTBO7iwm8hZ4ntQtBsMnnvybLC89tAoVXNE=
Date: Mon, 7 Oct 2013 07:06:17 +0000
Return-Path: 0000014191bce21d-5857cbb3-7185-4a04-a62d-02029457d42b-000000#amazonses.com
To: luca.pennisi#live.com
From: support BeAudience <support#beaudience.com>
Reply-To: support#beaudience.com
Subject: We remember you!
Message-ID: <0000014191bce21d-5857cbb3-7185-4a04-a62d-02029457d42b-000000#email.amazonses.com>
X-Priority: 3
X-Mailer: PHPMailer 5.2.6 (https://github.com/PHPMailer/PHPMailer/)
MIME-Version: 1.0
Content-Type: text/html; charset=UTF-8
Content-Transfer-Encoding: 8bit
X-SES-Outgoing: 2013.10.07-54.240.8.95
X-OriginalArrivalTime: 07 Oct 2013 07:06:18.0240 (UTC) FILETIME=[B83DF000:01CEC32B]
<html><head></head><body><b>Account
details:</b><p>username: tryHard<br />password:
porcodio</p><hr /><a
href="http://www.beaudience.com/joinus.php">Click
here to log-in</a><br /><br /><p>BeAudience
staff.</p></body></html>
I'm desperate, don't know what to do! I have configured SPF and DKIM but is useless! It not depends on the email content, I tried with different contents, html/non html but nothing to do with ses!!

It's not a problem on Amazon SES side, Microsoft filters are flagging your message based on multiple variables, like headers, content, domain age, etc.
That seems to be a Welcome Message, so the best way to go about it is to instruct the user to check the spam folder and mark the message as "not junk". Eventually and hopefully, Microsoft will learn from multiple user decisions and will start delivering your messages to the inbox.
Another advice, you are sending the message using PHPMailer. That header (X-Mailer: PHPMailer 5.2.6) may be triggering a flag on Microsoft side before even getting to your content.

I had the same problem. But I've fixed it. My steps:
add text/html version for mail;
check your html in email, make sure that is correct;
verify your domain in SES dashboard;

Related

Why does this particular message get delivered to the Junk mail of hotmail users?

I manage various servers that send and receive email at various levels. Mostly I use Sendmail on FreeBSD machines.
I'm having problems in delivering to Hotmail users and apparently more in general anyone that makes use of microsoft based antispam filters (I could be wrong here... it's my feeling).
Here are the headers of an email that was delivered to the Junk mail folder of a hotmail user. It was sent from a server of mine.
Received: from BL2NAM02HT013.eop-nam02.prod.protection.outlook.com
(10.172.93.15) by MWHPR11MB1775.namprd11.prod.outlook.com with HTTPS via
MWHPR1601CA0005.NAMPRD16.PROD.OUTLOOK.COM; Thu, 8 Feb 2018 10:09:59 +0000
Received: from BL2NAM02FT033.eop-nam02.prod.protection.outlook.com
(10.152.76.55) by BL2NAM02HT013.eop-nam02.prod.protection.outlook.com
(10.152.77.51) with Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384) id 15.20.444.13; Thu, 8
Feb 2018 10:09:59 +0000
Authentication-Results: spf=pass (sender IP is 148.251.12.94)
smtp.mailfrom=gmartandmusic.com; hotmail.com; dkim=pass (signature was
verified) header.d=gmartandmusic.com;hotmail.com; dmarc=pass action=none
header.from=gmartandmusic.com;
Received-SPF: Pass (protection.outlook.com: domain of gmartandmusic.com
designates 148.251.12.94 as permitted sender)
receiver=protection.outlook.com; client-ip=148.251.12.94;
helo=mail.europa.tuorlo.net;
Received: from mail.europa.tuorlo.net (148.251.12.94) by
BL2NAM02FT033.mail.protection.outlook.com (10.152.77.163) with Microsoft SMTP
Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384) id
15.20.444.13 via Frontend Transport; Thu, 8 Feb 2018 10:09:57 +0000
X-IncomingTopHeaderMarker: OriginalChecksum:3155FEC5C9D2530E959B4E07187F7D85EAB207E86B21DBD388EE2E71D188C39C;UpperCasedChecksum:68C64367B668FDE28564CAAC7801A9DF0B763468DCDE2B54A67FCFB40608C4EF;SizeAsReceived:1418;Count:12
Received: from auth (mail.europa.tuorlo.net [148.251.12.111]) by mail.europa.tuorlo.net (8.15.2/8.15.2) with ESMTPSA id w18A9qi2063516
(version=TLSv1.2 cipher=DHE-RSA-AES256-GCM-SHA384 bits=256 verify=NO)
for <yyyyyyyy#hotmail.com>; Thu, 8 Feb 2018 11:09:56 +0100 (CET)
(envelope-from xxxxxx#gmartandmusic.com)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=gmartandmusic.com;
s=europa; t=1518084596;
bh=Fw4LmErhAxOi/F7NxHoWyOX/LBhnx8rr2vjP9sF8wgs=;
h=From:Date:Subject:References:To;
b=smkwjTavx8NlQhBXyLGXWpLdYuPXc9qSqbkZ1DZJrnyLkNqUgfVkXmOtVGoC+Qzn9
Asn9V/Sb7EmPj6XJfnuXgTMtzz2pHb2J8oVY8t3A5ffO8k6V27k9yo/utNvmt8wuJX
Ozhyfn8CTmP6o1/Ak40QA5uwGuKSbEBWy/IyBYp+yPiyoWZ4r+LDTDGPwWUSVDrOD1
LjTCIwOtVvECw1OejxAe5aY+tluKjnEZIYEqawv8pSr3yznZJpdaDhuJF+3EtjtEBm
2iRsmG/tKzmZjQm5FQk66gZX4iwShAVgRPpxTmQ8bUR7qFR0sJ58F5iaOiXBi16bNc
ZU5m+VRtusqSQ==
From: AAAAAA BBBBBB <xxxxxx#gmartandmusic.com>
Content-Type: multipart/alternative;
boundary="Apple-Mail-89D34B6A-7702-4FBE-BCCD-41CBE90A98B6"
Content-Transfer-Encoding: 7bit
Date: Thu, 8 Feb 2018 04:09:52 -0600
Subject: Fwd: XXXXXX/XXXXXX/ MENORCA/ MAYO 2.021
Message-ID: <C8E45C6B-C6F6-43E9-A89F-511837A7ECFB#gmartandmusic.com>
References: <00A74997-678C-430C-89E0-F86081C7EF4D#infotelecom.es>
To: XXXX YYYY <yyyyyyyy#hotmail.com>
X-Mailer: iPhone Mail (15D60)
X-IncomingHeaderCount: 12
Return-Path: xxxxxx#gmartandmusic.com
X-MS-Exchange-Organization-Network-Message-Id: 35b1621c-5d7f-40d4-4ff6-08d56edc1ba6
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa:0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
X-Microsoft-Exchange-Diagnostics: 1;BL2NAM02FT033;1:hnTtkDvat2snlgurDQUVhYHckuMJhexw7rK/nMMILQql/P1hj3ZYszrvHlCTQ+cJV7wsMPwXfvp32kBc7HmUnj25fk1jbqqyJBW31tz9XQUHomlZtr7nZ+WhdGFNNRb8
X-Forefront-Antispam-Report: EFV:NLI;SFV:NSPM;SFS:(98901004);DIR:INB;SFP:;SCL:1;SRVR:BL2NAM02HT013;H:mail.europa.tuorlo.net;FPR:;SPF:None;LANG:;
X-MS-Exchange-Organization-AuthSource: BL2NAM02FT033.eop-nam02.prod.protection.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-PublicTrafficType: Email
X-MS-Office365-Filtering-Correlation-Id: 35b1621c-5d7f-40d4-4ff6-08d56edc1ba6
X-Microsoft-Antispam: BCL:0;PCL:0;RULEID:(5000109)(4604075)(4605076)(610169)(650170)(651021)(8291501071);SRVR:BL2NAM02HT013;
X-Microsoft-Exchange-Diagnostics: 1;BL2NAM02HT013;3:HFLkOvxb6v1otyVU+/4qGCI+fmLt/Wqog/HK8GHBqXEB3WB2/axCWD1jjLiZlE296Z8SYck6EVAxyuGrHKGKu1B4EME0OZmUxUyS5U8ekffZJkZPm02+XFw8rfWUEuJPbIKflo2V4k+kWwO9/pzmcZDyrTjVFNWzB7iqTt8fu3MFWaW0RBm+6+7xyqJPHnPjtvmvUer4Xgxr+GRqSrKS5rFeO5IV9HSY2oWsRz6VinE2HszPcTQnbjb1/fjxhwzDuZiKL2NFVi87Dngdx0jXBHTGyXnpi0LePdGJ6fKBRMrdCdrLT1C+IpB1N1A9iOGQ;25:vJ1cwnGFHXqKn2cvh2C4FZrvStWj3EMpztnpfl/Tjx4Qsa1NTyDBv3qV32gAKugMv61j+otmiaBwBt0bmOfZ03rGRrX7UcQ+rc7XTnyxkAJc0i8RoyrGn8AR8JeQ1mjXyWP1HXokKfC7yox6CzMk3JBjwYZMIA2tCOFf2XWDJcUKZa6j0qFX3SFJ0TzOU0zwh2M6o0l654csfZeRuacFF13XhDQjqtAVjhfquxN9zPuC/sHjNB/lG58SAcaQnPVdAGxmSaACqMy1PwpWNHog9db2n5d7Im8god9zgt46Js3HHOs5tYTQgapWXGqMB9542DS5MXeROtL3nKDJ0lZUQg==;31:xL0KY+h7mitOtfy4JrR1Ev3FihJLs0zekK/ska3dJvgZ2hENcSzd2szV5kYYrxOL0dDfHoUtWLwMdXQkICx5/TyUts4vNo1ZjX19LJEehfZLrJNIZ/aCw4Ay2U2BkVNFiOYsFAlTUfFUdfMFFI/Z8/SSkG5lP0sKEfMBgTBN/uvJ6NDqogj+3Wj2rTVw0xE5v36Lt+BhqEp7elVOFAsIEL5XT6lDuPrOM96JNLL5Lu8=
X-MS-TrafficTypeDiagnostic: BL2NAM02HT013:
X-MS-Exchange-EOPDirect: true
X-Sender-IP: 148.251.12.94
X-SID-PRA: xxxxxx#GMARTANDMUSIC.COM
X-SID-Result: PASS
X-MS-Exchange-Organization-PCL: 2
X-Exchange-Antispam-Report-Test: UriScan:;
X-Exchange-Antispam-Report-CFA-Test: BCL:0;PCL:0;RULEID:(444111557)(2400082)(82015058);SRVR:BL2NAM02HT013;BCL:0;PCL:0;RULEID:;SRVR:BL2NAM02HT013;
X-Microsoft-Exchange-Diagnostics: 1;BL2NAM02HT013;4:Bc5X2fSq55q6XMZsvCFLE4oHXKXL5AZAhAZGBUeXJfY75ES2dSXErxmc7xoNzyLA16U6a91wm46mrzllh+DwD6td0a7B+FqqTkZLMfw1UxZf35JsXmDdyLpU63rwjc/T0E/8hyY0Uinuu/zpC269Zae7IhV06dz4dMG1ZUdQmLVCwcJfsYsuF1ycgLsaeea9rfe5VJ0vzJRF5Kjwsp6/45sIzfAvjaM1NRWN28XIqgeC9KzjkrGCDHNBssMNPHEC6ARImdxUfWfPCa7TGhaxDA==;23:9ce9ZtosrYf8R0AWrHrwrH6nHRFGA0RUmqVTj/4SCDE5RgcC0sMp0bKixp8n2AgXIuRTV0ZTuKiqzKOA4i1mY4GkGMtuv0WAzOfbRDl5bkTbY5gp6dkZeqxu3/4xTP+zGc4GK5P1di8jaB231YLNUMBN9aUczu5IbOzyc6vBd8o=;6:+MLQPaxRIfraFLgoX3JjZbUA7ZFjMzePdr6IsDt9SCRZq2vdH/0bYZjMD5UEXCaw1+3fuJ8BQ/hFtJ69ZDoqmJc+4N7GWBYUN5sbbUg24PDa1W9hTzCAr1Av9O0LjBN1E/cvgX+9prrdUy1eD2HRtHNzkP+WIQrsIq+KjxZPhT9ysksd1ZuGHwwyFq3aK4RUsIDdhPr7LXiMsJJpmfxRgWxdXWu7adqzd72kPr09ldQ72iQ+fTWazynvogcTifDSElpLyysFQOMTGRKp4udakmsMOzpPp20YFMC0lTmHX0oScTk5OH4w0i7UdFJCAo/ehU4/re8J9GE5InXHWHsCoV0ZpJUg5jNDKFw0u30Gesg=
X-MS-Exchange-Organization-SCL: 1
X-Microsoft-Antispam-Message-Info: OuQazSvupgp80LHlw+czkqj2YXRxJ0QBIScl742vWOMdG2wzIGCcvnjwKv0mn6syMbpUBIwG+3E6FEILAAZOWcoHrSb+2pS/S97ZcRjDKt4=
X-Microsoft-Exchange-Diagnostics: 1;BL2NAM02HT013;5:1vihEbjfm4w0pm8T51O74gHVNQvaejj6rpVyRG4bmX78g6gAUqueSkb52YX+h4H2briNVccbLvBzptKLfqWtiYr1MZhMdfhigOtMyzM/76B73XZSirNN/wko+wf6Ba2iWqJVDIL10irMj1ege5KuK7y4jgPRa/6Nos1NBF3CWg8=;24:y257repAHT3J5K+9FAz+ju5GwAeDT9Dy7y1za4bcm8wV0fE1SQxow6DM6Sjt9r8iP68AD+/kbyR1Yc704J/7b5Ed3XTILDAseHK2XJu96JQ=;7:ua5Dt7PMVmi84xiS1h9BtzyLl7QLi6JC+r1rU5YjsN1Gw1plKnJMMYZ2V/xYZc9/rG34Dima4cYTl/BjfzSz73BlnAwL31YsfOPIAIiZPGP3Xb24QluF+Ev2B1dXWk8ytql7skz5beXvN237wl4qxzhaZ1hZJrnr33llGEfjl6PN0PIvoJhO2WSwMZze7j46rMHzB2qDCkzcieGNXhpnIr1r/WCNt35vKz6wJHfhi+cfOfSCnjoU7Wgzdwr8U6bp
SpamDiagnosticOutput: 1:99
SpamDiagnosticMetadata: NSPM
X-OriginatorOrg: outlook.com
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 08 Feb 2018 10:09:57.5256 (UTC)
X-MS-Exchange-CrossTenant-Network-Message-Id: 35b1621c-5d7f-40d4-4ff6-08d56edc1ba6
X-MS-Exchange-CrossTenant-Id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: BL2NAM02HT013
X-MS-Exchange-Transport-EndToEndLatency: 00:00:02.3696719
X-MS-Exchange-Processed-By-BccFoldering: 15.20.0485.002
X-Microsoft-Exchange-Diagnostics:
1;MWHPR11MB1775;27:44NdIk2HdVv/O8NpcZyQqTL8z9aaX2OM2n4+LxMT5Q/uFhT/kCDKFStN8D8BLF/slFIj5EQ4/+9TvCPMYrTSKknMgF0+VemHMyOmLboDCpjpHk+zI560m6NBXQT67cXm
X-Microsoft-Antispam-Mailbox-Delivery:
abwl:0;wl:0;pcwl:0;kl:0;iwl:0;dwl:0;dkl:0;rwl:0;ex:0;auth:1;dest:J;ENG:(400001000128)(400125000095)(5062000261)(5061607266)(5061608174)(4900095)(4920089)(6375004)(4950112)(4990090)(9140004);RF:JunkEmail;OFR:SpamFilterAuthJ;
X-Message-Info:
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X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Microsoft-Antispam-Message-Info:
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MIME-Version: 1.0
--Apple-Mail-89D34B6A-7702-4FBE-BCCD-41CBE90A98B6
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: quoted-printable
X-Microsoft-Exchange-Diagnostics:
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X-Microsoft-Antispam-Mailbox-Delivery:
abwl:0;wl:0;pcwl:0;kl:0;iwl:0;dwl:0;dkl:0;rwl:0;ex:0;auth:1;dest:J;ENG:(400001000128)(400125000095)(5062000261)(5061607266)(5061608174)(4900095)(4920089)(6375004)(4950112)(4990090)(9140004);RF:JunkEmail;OFR:SpamFilterAuthJ;
X-Message-Info:
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X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Microsoft-Antispam-Message-Info:
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The server is not blacklisted.
There are no reputation issues that I'm aware of.
The email just contained a simple threaded discussion between users.
We use SPF, DKIM and DMARC and they clearly all passed their respective checks from what I see in the headers.
Still it get's delivered in the Junk mail folder.
The email seems to be originated from an iphone and delivered to my sendmail based server. Then, on the hotmail side, it was apparently passed through an endless series of spam checks (judging by the redundancy of ms oriented antispam headers). They all agree it's not spam.
SFV:NSPM
SCL=1
BCL:0
PCL:0
SpamDiagnosticOutput: 1:99
SpamDiagnosticMetadata: NSPM
The only one that seems to disagree is this last "X-Microsoft-Antispam-Mailbox-Delivery" that shows a cryptic:
RF:JunkEmail
OFR:SpamFilterAuthJ
I was not able to find any documentation pertaining these codes. OFR could be "Offending Rule"? I don't know but the simple lack of documentation and answers is very annoying. What am I supposed to do? Tell my corporate clients "I'm sorry you can't deliver to microsoft based users?".
Any clues? Any ideas?
Have you checked the current ip status with postmaster SNDS of hotmail ?
There you could see 3 colours for ur ip. Red/Yellow/Green. Try to see the current status and build your reputation.

Increasing understanding of return-path and SPF records

I have a website with a web form that is hosted with a third party. I'm having trouble with their server config/architecture and wanted to confirm a few things and show the mail headers I am receiving.
I know that I must explicitly set my mail to send through an outgoing mail server and port which I have specified (this is in order for the mail to send, it will not be sent if not sent through the SMTP server).
Upon setting the SMTP server and port here is the mail header:
x-store-info:sbevkl2QZR7OXo7WID5ZcdV2tiiWGqTnhQzu7BHe69dd2ZvcRr0xBttv16txT0x/MHyyxbQQOWxD0k3WKrQDVl56gwTtl9T9YlQDKWZad3R7ZbliBL6BSfw52gpz37cwL/qGTahKP+U=
Authentication-Results: hotmail.com; spf=softfail (sender IP is 213.171.216.60) smtp.mailfrom=test#hotmail.co.uk; dkim=none header.d=hotmail.co.uk; x-hmca=fail header.id=test#hotmail.co.uk
X-SID-PRA: test#hotmail.co.uk
X-AUTH-Result: FAIL
X-SID-Result: FAIL
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0xO0Q9MTtHRD0xO1NDTD0y
X-Message-Info: NhFq/7gR1vSyCjVJ7Q2iIHhF9oW5eW+g+jrtzv+TwMhHX16XKDSEsIIxc1qXk1NO+AwFoToprpXBtEMxyoOvMnJSYUEEN4JngTWWsUg0/J3120nOI8GDZ8sF8m5iNGKuZt7Ds7svv3bOfUNBVLmpGlsbHUCNwXFNgry/rw0sWtsI0nyKa01KIdnxHDoLHp7GPP/klJGbBhJE2FLEW70tX5XZujwdcC9+R5m/pk5uo4uPxfmnwQK9yQ==
Received: from cust-smtp-auth1.fasthosts.net.uk ([213.171.216.60]) by BLU004-MC1F22.hotmail.com with Microsoft SMTPSVC(7.5.7601.23143);
Mon, 28 Dec 2015 05:59:03 -0800
Received: from fun-booths.co.uk (unknown [88.208.252.229])
by cust-smtp-auth1.fasthosts.net.uk (Postfix) with ESMTP id 923AF74021D
for <c_qatest#hotmail.co.uk>; Mon, 28 Dec 2015 13:59:02 +0000 (GMT)
Date: Mon, 28 Dec 2015 13:59:02 +0000
To: c_qatest#hotmail.co.uk
From: "test#hotmail.co.uk" <test#hotmail.co.uk>
Subject: Fun Booths - Booking form
Message-ID: <918f36d31bf876f19ea6d9563c1ad348#fun-booths.co.uk>
X-Priority: 3
X-Mailer: PHPMailer 5.2.10 (https://github.com/PHPMailer/PHPMailer/)
Reply-To: test#hotmail.co.uk
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit
Return-Path: test#hotmail.co.uk
X-OriginalArrivalTime: 28 Dec 2015 13:59:03.0161 (UTC) FILETIME=[E8B5FE90:01D14177]
Focusing on the Authentication-Results the (sender IP is 213.171.216.60) which is definitely the correct outgoing SMTP server. However the the spf result is spf=softfail.
After doing some research it was suggested that
The Return-Path header is empty. This means that during the SMTP
conversation, the MAIL FROM command did not specify an email address
where bounces are sent. It is the domain from this email address that
SPF tests. If there is no email address, a softfail will result.
Is this referring to the smtp.mailfrom field in the Authentication-Results which is set to a value of test#hotmail.co.uk in the example above?
I believe I have done what is required to implement SPF:
(1) I have set the SPF record in the domain's DNS zone
v=spf1 a ip4:213.171.216.0/24 mx -all
Now the confusion arises here. When someone else's mail server receives a message claiming to come from that domain, then
(2) the receiving server can check whether the message complies with the domain's stated policy
How does hotmail's receiving mail server for example do this check? because if I set a Return-Path of hello#fun-booths.co.uk then this results in spf=pass. Just to be clear www.fun-booths.co.uk is the domain being used.
x-store-info:J++/JTCzmObr++wNraA4Pa4f5Xd6uens6FBov4shFUrwGsQPla5CZKHNFpj4XdT2wfaqUtXggI++7RpfQIpooWW0Sp2ynYP894LLfhswpqbr+Di/ao+0Ofc9Btl/xdHLsTQXTk39KBE=
Authentication-Results: hotmail.com; spf=pass (sender IP is 213.171.216.60) smtp.mailfrom=hello#fun-booths.co.uk; dkim=none header.d=fun-booths.co.uk; x-hmca=pass header.id=hello#fun-booths.co.uk
X-SID-PRA: hello#fun-booths.co.uk
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTE7YT0xO0Q9MTtHRD0xO1NDTD0w
X-Message-Info: NhFq/7gR1vTQzco4wDfDIuNexRCLt7KFLQW7EkmNLn/2YehuSC93bNZTp87n+KmseY8TwxSqCjOondyBGOJR9CRbKyT/FU2B2nhMw3SU8HjmnNyAmDcRFqxvARiDy1lMz5O7U5B61WNdLZsDb1vLPQ93l4XO90mQcjMfCI4SWr50rtHEJwK9Y/c2zDWf8jdVXEgQOyBm4pQwu9z7isJFvrHl9HRMGMcWeNHQVVCsFOoqJ8mhQItxPg==
Received: from cust-smtp-auth2.fasthosts.net.uk ([213.171.216.60]) by SNT004-MC2F7.hotmail.com with Microsoft SMTPSVC(7.5.7601.23143);
Mon, 28 Dec 2015 06:05:27 -0800
Received: from fun-booths.co.uk (unknown [88.208.252.229])
by cust-smtp-auth2.fasthosts.net.uk (Postfix) with ESMTP id 66414740221
for <c_qatest#hotmail.co.uk>; Mon, 28 Dec 2015 14:05:26 +0000 (GMT)
Date: Mon, 28 Dec 2015 14:05:26 +0000
To: c_qatest#hotmail.co.uk
From: "hello#fun-booths.co.uk" <hello#fun-booths.co.uk>
Subject: Fun Booths - Booking form
Message-ID: <85119bedb602f9865290c2ea218315b4#fun-booths.co.uk>
X-Priority: 3
X-Mailer: PHPMailer 5.2.10 (https://github.com/PHPMailer/PHPMailer/)
Reply-To: test#hotmail.co.uk
X-Sender: hello#fun-booths.co.uk
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit
Return-Path: hello#fun-booths.co.uk
X-OriginalArrivalTime: 28 Dec 2015 14:05:27.0582 (UTC) FILETIME=[CDD7FBE0:01D14178]
This leads me on to my final questions - Is it true that the Return-Path must be set to a real email address on the site domain (www.fun-booths.co.uk), or mail will not send?
Because I have set up the mailbox hello#fun-booths.co.uk, however it seems even when I delete the mailbox that this still results in an spf=pass. It seems that in other words that not having a real email address on the domain, and instead just setting the Return-Path to hello#fun-booths.co.uk without the mailbox existing will result in an spf=pass. Should this be the case?
Is the email #fun-booths.co.uk set in the Return-Path used to determine the domain for the SPF checks?
Finally in the quotation above that mentions the SMTP conversation, is the MAIL FROM command referencing the smtp.mailfrom field in the Authentication-Results?
SPF Checks are always done with the envelope sender (MAIL FROM:) - smtp.mailfrom in your case. In the first mail you have test#hotmail.co.uk as envelope sender, but your server is not listed in the SPF record for hotmail.co.uk, and since that record has ~all as the last mechanism you get a Softfail.
In the second mail the envelope sender is hello#fun-booths.co.uk, so it's the SPF record for fun-booths.co.uk that is being used in that check.
So you should use a fun-booths.co.uk address as your envelope sender.
Depending on how you send mail from the web form there are different ways to control the envelope sender, but it may be that value of Return-Path is used as the envelope sender.
There don't have to be a mail-box for the envelope sender for the SPF to work, since SPF normally only look at the domain part of the address, but if the mail bounces somewhere in the process, the bounce message will normally be sent the the envelope sender, so it's a good idea to keep the mailbox for that address.

DMARC/SPF/DKIM not authenticating with third-party mail

We recently implemented a DMARC record for our domain:
"v=DMARC1; p=quarantine; pct=100; rua=mailto:me#mydomain.com"
(quarantine 100% of non-authenticated emails and send aggregate report to "me")
We use a third-party vendor to issue invites. The vendor sends email from invites#invites.vendordomain.com which is then sent through a mail relay "smtp3.mailrelaydomain.it". I also know that the mail relay uses a single ip address.
That address is included in our SPF record:
"v=spf1 ...[SNIP reference for other mail servers SNIP]... ip4:[ip address for the mail relay] ~all"
When I send an invite using the vendor's service, the message is quarantined.
When I view the aggregate DMARC report I see that the invite:
is recognized as being from an SPF-Authorized Server
passes raw SPF authentication for the sender's domain (invites#invites.vendordomain.com")
passes raw DKIM authentication for the mail relay domain (smtp3.mailrelaydomain.it)
Fails DMARC authentication for both DKIM and SPF for mydomain
Here is a sample headers from an invite.
BEGIN SAMPLE EMAIL HEADER
Delivered-To: someone#mydomain.com
Received: by 10.64.252.9 with SMTP id zo9csp100581iec;
Wed, 21 Oct 2015 11:40:13 -0700 (PDT)
X-Received: by 10.55.195.147 with SMTP id r19mr12995508qkl.12.1445452813709;
Wed, 21 Oct 2015 11:40:13 -0700 (PDT)
Return-Path: <invites#invites.vendordomain.com>
Received: from smtp3.mailrelaydomain.it (smtp3.mailrelaydomain.it. [ip for mail relay])
by mx.google.com with ESMTP id w15si9297939qha.131.2015.10.21.11.40.13
for <someone#mydomain.com>;
Wed, 21 Oct 2015 11:40:13 -0700 (PDT)
Received-SPF: pass (google.com: domain of invites#invites.vendordomain.com designates [mail relay ip] as permitted sender) client-ip=[mail relay ip];
Authentication-Results: mx.google.com;
spf=pass (google.com: domain of invites#invites.vendordomain.com designates [mail relay ip] as permitted sender) smtp.mailfrom=invites#invites.vendordomain.com;
dkim=pass header.i=#mailrelaydomain.it;
dmarc=fail (p=QUARANTINE dis=QUARANTINE) header.from=mydomain.com
Received: from FS-S05.vendorparentdomain.com (unknown [vendor parent ip])
(using TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits))
(No client certificate requested)
by smtp3.mailrelaydomain.it (Postfix) with ESMTPSA id 23387A0CBC
for <someone#mydomain.com>; Wed, 21 Oct 2015 15:07:35 -0400 (EDT)
DKIM-Signature: [DKIM Content]
Content-Type: multipart/alternative;
boundary="===============2166944298367943586=="
MIME-Version: 1.0
Subject: Please take our survey
From: Me <me#mydomain.com>
To: Someone Else <someone#mydomain.com>
Cc:
Date: Wed, 21 Oct 2015 18:39:48 -0000
Message-ID: <20151021183948.27448.90706#FS-S05.vendorparentdomain.com>
List-Unsubscribe: [unsubscribe link],
<mailto:invites#invites.vendordomain.com>
Reply-To: Me <me#mydomain.com>
X-Sender: invites#invites.vendordomain.com
I believe the issue is related to the from domain in the message not matching the domain for the message envelope; however, the vendor is unable to change their settings (i.e., envelope will always be from the vendor domain) so any chance of this working with DMARC will have to come from my end.
Knowing that the SPF record can (and does) identify the invite as being from an SPF-Authorized Server, are there any other settings or records I can add to also ensure DMARC authentication for invites from the vendor?
Having read several online articles and "DMARC -spf and DKIM record queries" I suspect I am out of luck, but need to ask the question plainly/specific to my situation just to be sure.
Thanks
You are correct, you are out of luck unless the vendor can change something. What is failing is Identifier Alignment - https://www.rfc-editor.org/rfc/rfc7489#section-3.1 - because what is being authenticated (invites.vendordomain.com via SPF) does not align to the domain the user sees (me#mydomain.com) and the message then, correctly, fails DMARC.
There are three options:
Stop sending with a From: header of your domain at the vendor; you can still use a Reply-To: header with your own address.
Have the vendor align the mail from to your domain. If they don't do this they can't pass DMARC, and at some point they will want to pass DMARC or people will find other solutions. You can have them send with an envelope from of vendorname.mydomain.com and you can set up an MX for that subdomain that points to them to support bounce processing. This has been BCP for a while.
Have the vendor sign with DKIM and us an aligned DKIM signature. This is also best common practice. You only need SPF or DKIM to pass, and DKIM passes are more valuable (because they survive forwarding in many cases) than SPF, so this is the option I would personally prioritize if I were you.
Back in like 2012 and 2013 a lot of vendors pushed back against both of these options, but I honestly haven't seen a vendor in a long time (I spend 100% of my day job on DMARC) that won't support at least aligned DKIM.

Identify spam indicators based on emails headers

Using PHPMailer with SMTP, the following email was sent from my VPS (mydomain.com hosted by phpwebhosting) as if it came from my Comcast account (jane.doe#comcast.net) to my Gmail email (john.doe#gmail.com), and Gmail flagged it as spam.
Looking at the email headers, how can I determine what might make a email client flag an email as spam?
Delivered-To: jane.doe
Received: by 10.28.7.197 with SMTP id 188csp518471wmh;
Fri, 8 May 2015 06:51:39 -0700 (PDT)
X-Received: by 10.43.17.135 with SMTP id qc7mr4244827icb.14.1431093098853;
Fri, 08 May 2015 06:51:38 -0700 (PDT)
Return-Path: <john.doe#comcast.net>
Received: from smtp1.phpwebhosting.com (smtp1.phpwebhosting.com. [145.242.148.75])
by mx.google.com with SMTP id ag10si4096698icc.25.2015.05.08.06.51.38
for <jane.doe>;
Fri, 08 May 2015 06:51:38 -0700 (PDT)
Received-SPF: neutral (google.com: 145.242.148.75 is neither permitted nor denied by domain of john.doe#comcast.net) client-ip=145.242.148.75;
Authentication-Results: mx.google.com;
spf=neutral (google.com: 145.242.148.75 is neither permitted nor denied by domain of john.doe#comcast.net) smtp.mail=john.doe#comcast.net;
dmarc=fail (p=NONE dis=NONE) header.from=comcast.net
Received: (qmail 29774 invoked from network); 8 May 2015 13:51:37 -0000
Received: from unknown (HELO test.sites.mydomain.com) (outgoing#mydomain.com#145.242.134.91)
by smtp1.phpwebhosting.com with (DHE-RSA-AES256-SHA encrypted) SMTP; Fri, 08 May 2015 09:51:37 -0400
Date: Fri, 8 May 2015 06:51:36 -0700
To: Jane Doe <jane.doe>
From: John Doe <john.doe#comcast.net>
Reply-To: john.doe#comcast.net
Subject: Mydomain Password for Test Site
Message-ID: <fa1b444df47091d2ca100f40d93b14cc#test.sites.mydomain.com>
X-Priority: 3
X-Mailer: PHPMailer 5.2.9 (https://github.com/PHPMailer/PHPMailer/)
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="b1_fa1b444df47091d2ca100f40d93b14cc"
Content-Transfer-Encoding: 8bit
--b1_fa1b444df47091d2ca100f40d93b14cc
Content-Type: text/plain; charset=us-ascii
Hello Jane,
I have added you to our Mydomain sales tracking and bid solicitation tool.
Your username is: jane.doe.
Click the following link within 24 hours to set your password: https://test.sites.mydomain.com/index.php?cid=25&task=display_p&t=28dba87d5fb8062e40a69f0192660471
Thank you
--b1_fa1b444df47091d2ca100f40d93b14cc
Content-Type: text/html; charset=us-ascii
<p>Hello Alvin,</p>
<p>I have added you to our Mydomain sales tracking and bid solicitation tool.</p>
<p>Your username is: jane.doe.</p>
<p>Click the following link within 24 hours to set your password: https://test.sites.mydomain.com/index.php?cid=25&task=display_p&t=28dba87d5fb8062e40a69f0192660471</p>
<p>Thank you</p>
--b1_fa1b444df47091d2ca100f40d93b14cc--
There is no surefire way to tell why Gmail flags an email as spam. Spam filters in general are black boxes from the perspective of the sender, as only those who know the inner workings and have access to logs can tell for sure what happened to certain email. The reason for flagging can be virtually anything, like violating the sender domain's policies, poor IP reputation, poor reputation of links used, similarity to spam emails, bad standards compliance and so on. Sometimes there is no singular reason either.
It's not that you can't make an educated guess. In this particular case, you are sending an email in the name of a comcast.net user, but you are bypassing Comcast servers entirely. Comcast has SPF and DMARC policies in place and although Comcast's SPF policy evaluation doesn't assert smtp1.phpwebhosting.com either permitted or not (SPF "neutral" result), the DMARC result that Gmail is getting is "fail". The DMARC policy for Comcast is not to flag emails failing email authetication (but report them only), but I'd still guess it's a bad omen. Try sending the email via your authorized Comcast server or use your own domain name for both From: and Return-Path to see if you can avoid getting flagged as spam.

email that my application sends is getting spammed: what's wrong with my headers?

I'm sending out emails via my PHP application. However, they're getting marked as spam by Gmail. Here's how I'm sending the email (PHP):
$headers = "From: test#bookmytakeout.com\r\nReply-To: test#bookmytakeout.com";
$mail_sent = mail( 'munged#gmail.com', 'test mail', $message, $headers, '-ftest#bookmytakeout.com' );
Gmail spams this message. So I went and clicked that handy "show original message" option. Here's what I get:
Delivered-To: munged#gmail.com
Received: by 10.68.71.200 with SMTP id x8cs325812pbu;
Thu, 21 Jul 2011 01:34:52 -0700 (PDT)
Received: by 10.236.114.234 with SMTP id c70mr12483739yhh.163.1311237292052;
Thu, 21 Jul 2011 01:34:52 -0700 (PDT)
Return-Path: <test#bookmytakeout.com>
Received: from vps.bookmytakeout.com ([8.22.200.47])
by mx.google.com with ESMTPS id u61si3662037yhm.119.2011.07.21.01.34.50
(version=TLSv1/SSLv3 cipher=OTHER);
Thu, 21 Jul 2011 01:34:51 -0700 (PDT)
Received-SPF: neutral (google.com: 8.22.200.47 is neither permitted nor denied by best guess record for domain of test#bookmytakeout.com) client-ip=8.22.200.47;
DomainKey-Status: bad format
Authentication-Results: mx.google.com; spf=neutral (google.com: 8.22.200.47 is neither permitted nor denied by best guess record for domain of test#bookmytakeout.com) smtp.mail=test#bookmytakeout.com; domainkeys=neutral (bad format) header.From=test#bookmytakeout.com
DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws; s=default; d=bookmytakeout.com;
h=Received:To:Subject:From:Reply-To:Message-Id:Date;
b=WYWQ+/9+wOAvq+OUSM5KLDAueciIoNiByXaVV29HYa0XbSwm2f+89TCj8pW24G7k1vTGCvR8n64iSwgPQuoEitz6ehbszd0+75Px0WlGsvyeZGrW3PaYEpkRFmkDoaGe;
Received: from munged by vps.bookmytakeout.com with local (Exim 4.69)
(envelope-from <test#bookmytakeout.com>)
id 1QjolW-0001Vn-Us
for munged#gmail.com; Thu, 21 Jul 2011 14:07:31 +0530
To: munged#gmail.com
Subject: test mail
From: test#bookmytakeout.com
Reply-To: test#bookmytakeout.com
Message-Id: <E1QjolW-0001Vn-Us#vps.bookmytakeout.com>
Date: Thu, 21 Jul 2011 14:07:30 +0530
X-AntiAbuse: This header was added to track abuse, please include it with any abuse report
X-AntiAbuse: Primary Hostname - vps.bookmytakeout.com
X-AntiAbuse: Original Domain - gmail.com
X-AntiAbuse: Originator/Caller UID/GID - [1005 1000] / [47 12]
X-AntiAbuse: Sender Address Domain - bookmytakeout.com
test
Now, I have no idea how to diagnose what could be setting off gmail's spam filters. Can someone please point out what part of this email is setting off the spam filter?
If possible, please post a solution as well. I'm more interested in learning what's wrong with the headers than in how to fix this for now.
PS: I have a few suspicions of my own:
the Received header says "vps.bookmytakeout.com" but the From header says "bookmytakeout.com" - but I tried sending it with From as test#vps.bookmytakeout.com - same problem, still spammed.
The headers "Received-SPF", "DomainKey-Status" and "Authentication-Results" seem to indicate some problem. I distinctly remember NOT setting up any MX records for this domain name. Could that be the issue?
I guess you didn't publish any SPF / DKIM authentication record
Received-SPF: neutral (google.com: 8.22.200.47 is neither permitted nor denied by best guess record for domain of test#bookmytakeout.com) client-ip=8.22.200.47;
DomainKey-Status: bad format
Most of the time, Gmail (as well as the other major ISPs) will place the non-authenticated messages in the junk folder.
An SPF record or a DKIM guarantees that you are allowed to use a certain domain as a sender. For example, if you don't own "paypal.com", you can't send an email from "contact#paypal.com". If you've published the right SPF / DKIM, the ISP will consider you as a trusted sender.
SPF & DKIM were first designed to fight against phishing.
DIY SOLUTION: Publish some records by following these instructions:
http://dkim.org/specs/rfc5585.html
http://www.openspf.org/FAQ
EASY SOLUTION: Use a service that will do everything for you. A good ESP will usually sign your emails with DKIM / SPF by default. The problem is that you will sometimes get a "sent via ESP_NAME" mention (in Gmail).
So the best thing to do is to choose an ESP which will provide you personalized DKIM & SPF. This way, it will be 100% transparent.
I work for Mailjet and we offer this service for free. Most of our competitors offer this as an option.
Here's a useful post about this "via-mention" you get when your ESP signs "by default" and how to get rid of it.
http://blog.mailjet.com/post/16922561593/personalized-spf-dkim