Issue Outgoing emails marked as Spam on Hotmail and Yahoo

[Marten Vaino]

Hi,

I am having problems with outgoing emails. Email servers seem to be working fine, receiving emails is not a problem and sending is also OK, but Hotmail and Yahoo mark the emails sent by my Plesk server as spam. I tried other smaller email services as well and they do not mark them as spam. Gmail seems fine, though it sent to spam previously.

My server hostname: myserver.com

This is the message source sent by email "[email protected]" -> "[email protected]":
I replaced the server original IP with 12.345.67.890 and hostname with myserver.com

Received: from CY1NAM02HT088.eop-nam02.prod.protection.outlook.com
(2603:10a6:802:2b::43) by VI1PR0901MB1325.eurprd09.prod.outlook.com with
HTTPS via VI1P190CA0030.EURP190.PROD.OUTLOOK.COM; Fri, 30 Mar 2018 16:35:39
+0000
Received: from CY1NAM02FT058.eop-nam02.prod.protection.outlook.com
(10.152.74.60) by CY1NAM02HT088.eop-nam02.prod.protection.outlook.com
(10.152.74.74) with Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384) id 15.20.631.7; Fri, 30
Mar 2018 16:35:38 +0000
Authentication-Results: spf=pass (sender IP is 12.345.67.890)
smtp.mailfrom=myserver.com; outlook.com; dkim=pass (signature was verified)
header.d=myserver.com;outlook.com; dmarc=pass action=none
header.from=myserver.com;
Received-SPF: Pass (protection.outlook.com: domain of myserver.com designates
12.345.67.890 as permitted sender) receiver=protection.outlook.com;
client-ip=12.345.67.890; helo=myserver.com;
Received: from myserver.com (myserver.com) by
CY1NAM02FT058.mail.protection.outlook.com (10.152.74.149) with Microsoft SMTP
Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384) id
15.20.631.7 via Frontend Transport; Fri, 30 Mar 2018 16:35:37 +0000
X-IncomingTopHeaderMarker: OriginalChecksum:A51C0430C92E10CBF0CB885E334B67726C4A1F2EBBA146B74E91CB267A1E5855;UpperCasedChecksum:D91F9AF9C58A33C769DECCEA6C0569608F6AF64449AF3655426D7B84A94EFA52;SizeAsReceived:1139;Count:14
Received: from webmail.myserver.com (localhost.localdomain [127.0.0.1])
by myserver.com (Postfix) with ESMTPA id DFFC43D610C3
for <[email protected]>; Fri, 30 Mar 2018 18:35:35 +0200 (CEST)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=myserver.com;
s=default; t=1522427735;
bh=2MK3fzvQQLCX0MZXdiwBshtaVpId0xGStWsy7IO5By4=; l=56;
h=From:To:Subject;
b=SO9BVlQxBG9+wDkMBkoIx7yUgCnOspwYBNFp9USCdp5N26mqM96Dc0jpOt3AG46C0
NxEbFFVapWTeAPZLZFSDEDQrH/9/xYxFL1VNlSIOur2bmojmxhpa3wrNfewEmAxJpP
MztvIY+0O/qXfWA5N3OgyHaN4DKGtlenYLY4l8pE=
Authentication-Results-Original: myserver.com; spf=pass (sender IP is
127.0.0.1) [email protected] smtp.helo=webmail.myserver.com
Received-SPF: pass (myserver.com: connection is authenticated)
Content-Type: text/plain; charset="US-ASCII"; format=flowed
Content-Transfer-Encoding: 7bit
Date: Fri, 30 Mar 2018 19:35:35 +0300
From: Marten Vaino <[email protected]>
To: [email protected]
Subject: Letter to see if the mail works
Message-ID: <[email protected]>
X-Sender: [email protected]
User-Agent: Roundcube Webmail/1.2.7
X-IncomingHeaderCount: 14
Return-Path: [email protected]
X-MS-Exchange-Organization-Network-Message-Id: c18d7fb5-55ff-4074-af55-08d5965c44b7
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa:0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
X-Microsoft-Exchange-Diagnostics: 1;CY1NAM02FT058;1:7cmpwr3jy0hxsdeBaGe5sqL29auF7uXnnX/ZigVEWQpfi1tO9uG/1M5Gdfblph9DBtpTyXLVEzLsfIXPQ4aGcUxoZ6TAwx/5a72OjhyGvsySGhONotRSJsdS6l6NlALm
X-Forefront-Antispam-Report: EFV:NLI;
X-MS-Exchange-Organization-AuthSource: CY1NAM02FT058.eop-nam02.prod.protection.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-PublicTrafficType: Email
X-MS-Office365-Filtering-Correlation-Id: c18d7fb5-55ff-4074-af55-08d5965c44b7
X-Microsoft-Antispam: BCL:0;PCL:0;RULEID:(5000109)(4604075)(4605076)(610169)(650170)(651021)(8291501071);SRVR:CY1NAM02HT088;
X-Microsoft-Exchange-Diagnostics: 1;CY1NAM02HT088;3:BEOrjbsLGFaDUFQTrO2p2phA1XQ6UbaDIa7x30+LmUgi2pa+Yg69y/ieawISexLlXqbRQuSI782r8uJrnGYOM3DyxOMKQ0MgCnG6B6orpGw0fypXGaCsdP03LFEre4VzxhNQC27ZOhDfiXTgEElJtm67JGp6uhIFhUFjj7Z2t918d5qubeSVz1Cr/Pzf+ztRqe9fi/9ZPUiCxHyWwJrju4a2fwH/NZC0AYnjdNL4O3RVhaWmsQHqGybc2HFii+vTqK8igH7rGYYj7srN75vcizu2PHq+hsLaE5BVkBGCrnCieB4boxr+E86QK9BB+qdX;25:0HByPecHrIM3n3Ly33znSLmlKIJnzHnGMy8RR4yRhLOQofbkpm/0Jo59Uk+/aa1thvdRo11JuADTDJ1qDAHPEvIqIxsUhFr4YGxMipmHZ5a9SnSz5fTb7YCbsie+uvS/vnRhCpk84+y4/a8me6/FLtRxaW+8kubicFv1Rajt0qk+Fnzud5eNrz0DPor6lzbRF0N2bOHLLiKh6Fak2K2NkEwhZKfzyY+nANhK/47Q84jm9F/+Y4hzP8tOYZRJpDaLc8xj/YJ69vGUPvbUBh4QS2mqUU5muCqBwBxgAYsYAbUgoeWvQ/Zc+/DMxKylm1R70Xph1797GEN+GnrLL02PzQ==;31:4lmtXqy+nXYu0yLfU84p+8bl0hVQ896BQAKfJlmrskK8B02xEZ6ofYEj5jAPogKguoNm7k+oJjuTuyw3PyIIm5IX+D2c5r86FjWytAr6tlvZHXMBQi7gYXF10Q/zSIhi8jLNRu0apB2cgCebiWjE2z3w4pv07h9L8h5V6IAPtc8uikkUkh/RAGLn6tEuRdjbrIhd0zIJme2S+8scdi7ULeaRDxRfw1cB3+Yxwau/z/M=
X-MS-TrafficTypeDiagnostic: CY1NAM02HT088:
X-MS-Exchange-EOPDirect: true
X-Sender-IP: 12.345.67.890
X-SID-PRA: [email protected]
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:(444111676)(52104095)(52401095)(52601095)(52505095)(52406095)(82015058);SRVR:CY1NAM02HT088;BCL:0;PCL:0;RULEID:;SRVR:CY1NAM02HT088;
X-Microsoft-Exchange-Diagnostics: 1;CY1NAM02HT088;4:n+unmGnVuhPxWD4nt5hBxoLPzKsUN7EkzpzZu0GIcSXh1GL7eDFxNWGZor+m65XXo2wYSj3nDq53ddJOVUurOm5ZRFPltU1sSv7dsOjthZYPxtOGJo4OvsXf5MJX51Idmp1D33qCeLhqNYtlAmQyIC+E45geUon4+5tNRCakHr7NdAKaSoBBzff0mCBb87jkDJEgqKHWDxKfo0zAkzL9nT3zZKOcnPC56pVlTlsjMqUOdZQe66+UlAIu8Bn6tKKUitc54LcgmZB5e1n+RoEyTQ==;6:ehvH/Rn4N9rDxwMUE7x8MCn7fevt0MEcu2nJtNDaPJb5RiG5KmysMWKTN7rheKv3wsOp9k2YCEFLhqAuQT7fK0xFAi28/feDmfFqaZVkvSthSn6lsixfcle9uHl832vpjJb1eYNRB/gVUGnYzrB3Qjww0IEbPNkLs2F+68Tdx20I/6+LWaZ+gpg+pE2OGV9K6u5GII72Qmja0cxHwuZ5zliyCKl7hTiJ5jcaRdE3BOb91/KjDIsKbqSufxOaNYUtoDyZBlTOOIkutk3oRqYJ1AzNORbh+5ZyMfShbKe5VgKH0yotmvK0pyKwiRD8j3VEcASZhcRag9/E+mMp/OTtsHKti5DEj1P3W3k+m/firXwuz/h1T2Jye4iS5QXycqdpLlbP7jdGlsLyBmzmz0Jihujqm9fizaHMqco68HE6jZbV7+v5/LA1nE5Llqj1V3N0qPjq0Kc7hWWIUCppKf7rBA==;5:POz5+w3XlhzJ8nhIE0rKECZT9FyYVv1sQztuXyOP2lo1lFZJlBIsoog8GXGRluHYwkgA5X6rLHjLBJG9pj86Qjc3r4TXtaN/UzGTadcbS0S3AsZteR5n9vl/Omupnw/2DnY9036TSPn6yPVWbgLju9HLay1j+79FAauWHPJOg2Y=
X-Microsoft-Antispam-Message-Info: 4ZDRDbfWD9WhNapqlUwrmqPTLvtYZJz1BPzE6lCanBFTnIFu675TynskQCqhPS1Ohzc98YNKoxBRLl2zAuisHsO3YHVYuSNCMIE7g7BVCnpIRD0fCPYOJG7UJbzCtSkh45gMPe6TAvRhY1eN0JZfbkdfdrI7hYR+lbrmMwixAxw8xJ2kuCsBswX8QBCh5h/k
X-Microsoft-Exchange-Diagnostics: 1;CY1NAM02HT088;7:FYT1kz3x9jeOtmIZ42EdN5wsvLmPKNujvVYpVHdmfFOmT96dBvb7NoxRuHO2dreNYvx2dE1ZtwP0wrci7I9Ji+dZABLrLizNcHW4D6cPBmA6OONck459HXkumrxUO67vbnxpAxiDEw3ju38Ju3BTqF7U+SorUxPMwbLs56UUvb1h3dzSaCCas5Micl7XLr+fKuZ7R5Uk3DUdW3T2mpgWb5FghM+Z3Hu/vKg0IJT92Vf2acaZIiNu9iIDJOMC+aYk
X-OriginatorOrg: outlook.com
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 30 Mar 2018 16:35:37.4651
(UTC)
X-MS-Exchange-CrossTenant-Network-Message-Id: c18d7fb5-55ff-4074-af55-08d5965c44b7
X-MS-Exchange-CrossTenant-Id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: CY1NAM02HT088
X-MS-Exchange-Transport-EndToEndLatency: 00:00:01.7380060
X-MS-Exchange-Processed-By-BccFoldering: 15.20.0609.000
X-Microsoft-Exchange-Diagnostics:
1;VI1PR0901MB1325;27:khNERNvzVmgJ6vsTX0drFBnmatYUdMVOOvfr5xGbrcuN8SfjdBM1aUDLyOdPUfVQzUz4lVP0D6BlnVNHpreNIcicpzq/uD2drCOF4vjmsoG1oZgoI/3q6ggb8JGbPALF
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)(4950130)(4990090)(9140004);RF:JunkEmail;OFR:SpamFilterAuthJ;
X-Message-Info:
qoGN4b5S4yrmAeNVLAMFDslnOcoUsFCaH3ZBO/myiGJanS2jv0IhczFJucaNZOHg42zMAwEvnwh8DP63Wf6cx4DiDkAlaEYyavfl+L4T/743P6lRxeIZW4gq5QYImi5b+LZ4OYrS1FtWRamSvG+WXnPawr2w1zWfcdv1sPQEY4gNUMIIMqCzWWPor/P+pUVlugcTPM+ouoQOCHZclsnM4w==
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Microsoft-Antispam-Message-Info:
7S49/bKjrwcE7rvKjC7Q8904rFauLUhdkZU1Hf1pG05es1nFVjhmS7Lz6346j5oSyGFPna96Vz+w7cRIOzkxGjhCPfPLMVmQv6fN2fhORgQzc0ZZDEwswfOfpVY5iZiF1G9t45U44wLd0uEtGc6JAsa6Xiw7kITdThMieWgmLpGiL1yHDRFIuw5PpfV/Rbg9Sz5qfm/XyMdG1Cl3sfUSlVlNcSBL305vCfSyqXm3ZdjgGM2O3EmBh3e5VPdzvQsbbZl0ekVj3YQ27BydQUw+a5pseMXCQzbI+ifMbCfySVzsN3tVhjRUrkYzu6lh5NtuDTnTlypCVUMco0h2KlHMlGmELqib0Xu7PFHzEtmF/o8=
MIME-Version: 1.0

This is a test to see if it works.

Regards,
Marten

I also did test with mail-tester.com and got a result 10/10:
[SPF] Your server 12.345.67.890 is authorized to use [email protected]
Your DKIM signature is valid
Your message passed the DMARC test
Your server IP is successfully associated with myserver.com
Your domain name myserver.com is assigned to a mail server.
Your hostname myserver.com is assigned to a server.

Also checked multiple spam check sites and it is a clean IP address and a clean domain name.

The DNS settings for myserver.com are as following:
myserver.com. TXT v=spf1 a mx ~all
myserver.com. MX(10) mail.myserver.com.
mail.myserver.com. A 12.345.67.890
myserver.com. A 12.345.67.890

---

/etc/postfix/main.cf:
inet_protocols = ipv4
inet_interfaces = all
myhostname = myserver.com

Additional question - is it OK if I create a subscription for my customer and their mail server configuration is MX: mail.theirdomain.com (not mail.myserver.com?). Right now it is not an external mail server.

With all of these configurations my emails go to spam (Gmail seems fine now, but Hotmail/Outlook and Yahoo still think it is spam). I've been pulling my hair out for the last couple of days, does anyone have idea what the problem could be?

 

[Marten Vaino]

Noticed an another issue right now, which might be related. I created a subscription for my customer (let's say customer.com) and they made an email [email protected] and forwarded this email to a [email protected] email address. Now when they sent an email to [email protected], it arrived to Gmail but it was marked as spam. If the email is sent directly to gmail address, it is fine.

 

[AYamshanov]

Hi Marten,

1) "[email protected]" -> "[email protected]". Looks like your server was configured correctly. Did you ask Hotmail/Yahoo why such emails marked as spam?

2) "[email protected]" forwarded to a "[email protected]". I suggest not mixing different question in one thread. Could you please create a new thread? Is it an automatic forward? Could you post email headers for email marked as spam in Gmail?

 

[Marten Vaino]

I asked Outlook for information and received this:
- Our investigation has determined that the above IP(s) do not qualify for mitigation.
- We have reviewed your IP and determined that messages are being filtered (i.e. sent to the Junk folder) based on the recommendations of the SmartScreen® Filter. Unfortunately, after reviewing the information you provided and in compliance with our mail policies, we are unable to offer immediate mitigation for your deliverability issue.

Is it possible to setup an external SMTP server for only emails, so that I will continue to use the same server as web hosting, but outgoing mail is sent using a server that has a "more trusted IP"? Will I need to install Plesk on another server, how will the accounts sync?

 

[seqoi]

I had similar problems but as soon as i started to force valid DKIM and SPF in my customer emails all problems went away.

 

[G J Piper]

Noticed an another issue right now, which might be related. I created a subscription for my customer (let's say customer.com) and they made an email [email protected] and forwarded this email to a [email protected] email address. Now when they sent an email to [email protected], it arrived to Gmail but it was marked as spam. If the email is sent directly to gmail address, it is fine.

This sounds like the issue from this post: Issue - DMARC issue with forward mail
There may (or may not) be some help at that thread.