Issue All my emails go to Spam (Hotmail - Outlook)

[Sergio Sánchez]

Hello.

I have installed plesk on my new VPS Server. All run correctly but my emails go to spam in Hotmail. This only happen with hotmail - outlook. Gmail and other providers run correctly.

The headers show:

Mensaje de prueba

Este mensaje se identificó como spam. Lo eliminaremos dentro de 10 días. No es spam
[email protected]
Mié 20/02/2019 2:57
Mensaje de prueba
Received: from HE1EUR01HT023.eop-EUR01.prod.protection.outlook.com

(2603:10a6:4:54::30) by DB7PR03MB3673.eurprd03.prod.outlook.com with HTTPS

via DB6PR0301CA0062.EURPRD03.PROD.OUTLOOK.COM; Wed, 20 Feb 2019 10:57:53

+0000

Received: from HE1EUR01FT028.eop-EUR01.prod.protection.outlook.com

(10.152.0.57) by HE1EUR01HT023.eop-EUR01.prod.protection.outlook.com

(10.152.0.242) with Microsoft SMTP Server (version=TLS1_2,

cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384) id 15.20.1580.10; Wed, 20 Feb

2019 10:57:53 +0000

Authentication-Results: spf=pass (sender IP is XXX.XXX.XXX.XX)

smtp.mailfrom=mydomain.com; hotmail.es; dkim=pass (signature was verified)

header.d=mydomain.com;hotmail.es; dmarc=pass action=none

header.from=mydomain.com;

Received-SPF: Pass (protection.outlook.com: domain of mydomain.com designates

XXX.XXX.XXX.XX as permitted sender) receiver=protection.outlook.com;

client-ip=XXX.XXX.XXX.XX; helo=mail.mydomain.com;

Received: from mail.mydomain.com (XXX.XXX.XXX.XX) by

HE1EUR01FT028.mail.protection.outlook.com (10.152.0.157) with Microsoft SMTP

Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id

15.20.1580.10 via Frontend Transport; Wed, 20 Feb 2019 10:57:53 +0000

X-IncomingTopHeaderMarker: OriginalChecksum:037973593832310761503B90DA185CC6AC57581D117953A8FB5F10791C74F76A;UpperCasedChecksum:5CA28CD7D9F64E2BA4084AC34A89347B4D03CD9D3788E6CAAAB6B4C9371BAC8B;SizeAsReceived:1139;Count:14

Received: from webmail.mydomain.com (localhost.localdomain [127.0.0.1])

by mail.mydomain.com (Postfix) with ESMTPSA id 8491283053

for <[email protected]>; Wed, 20 Feb 2019 11:57:52 +0100 (CET)

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mydomain.com;

s=default; t=1550660272;

bh=7faiHJm4BZp5xMOsxHz5sf847ZjJplWEtC0KOQyZb1A=; l=19;

h=From:To:Subject;

b=TbRIJ+WfzHCQd3hARkyTpLSUwUru/wyEcx9YItAX4fsmaHD24m7hzXJ6SikbpinsR

emimwe5owt/gR/vT/b/rz2Ohu3JAdLG0iXIXVCI+TZ4CRdwgOUX2thEi30MkKzXVbI

7cN9KReIflajlZXAj7MVlpgXPUB0A5ASsPtuPRes=

Authentication-Results-Original: mail.mydomain.com; spf=pass (sender IP

is 127.0.0.1) [email protected] smtp.helo=webmail.mydomain.com

Received-SPF: pass (mail.mydomain.com: connection is authenticated)

Content-Type: text/plain; charset="US-ASCII"; format=flowed

Content-Transfer-Encoding: 7bit

Date: Wed, 20 Feb 2019 11:57:52 +0100

From: [email protected]

To: [email protected]

Subject: Mensaje de prueba

Message-ID: <[email protected]>

X-Sender: [email protected]

User-Agent: Roundcube Webmail/1.3.6

X-IncomingHeaderCount: 14

Return-Path: [email protected]

X-MS-Exchange-Organization-ExpirationStartTime: 20 Feb 2019 10:57:53.1587

(UTC)

X-MS-Exchange-Organization-ExpirationStartTimeReason: OriginalSubmit

X-MS-Exchange-Organization-ExpirationInterval: 2:00:00:00.0000000

X-MS-Exchange-Organization-ExpirationIntervalReason: OriginalSubmit

X-MS-Exchange-Organization-Network-Message-Id: 9a8c2bf3-2724-4c67-c750-08d697224332

X-EOPAttributedMessage: 0

X-EOPTenantAttributedMessage: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa:0

X-MS-Exchange-Organization-MessageDirectionality: Incoming

X-Forefront-Antispam-Report: EFV:NLI;

X-MS-Exchange-Organization-AuthSource:

HE1EUR01FT028.eop-EUR01.prod.protection.outlook.com

X-MS-Exchange-Organization-AuthAs: Anonymous

X-MS-PublicTrafficType: Email

X-MS-UserLastLogonTime: 2/20/2019 10:56:08 AM

X-MS-Office365-Filtering-Correlation-Id: 9a8c2bf3-2724-4c67-c750-08d697224332

X-Microsoft-Antispam:

BCL:0;PCL:0;RULEID2390118)(5000110)(711020)(4605104)(610169)(650170)(651021)(8291501071);SRVR:HE1EUR01HT023;

X-MS-TrafficTypeDiagnostic: HE1EUR01HT023:

X-MS-Exchange-EOPDirect: true

X-Sender-IP: XXX.XXX.XXX.XX

X-SID-PRA: [email protected]

X-SID-Result: PASS

X-MS-Exchange-Organization-PCL: 2

X-Exchange-Antispam-Report-CFA-Test:

BCL:0;PCL:0;RULEID444111751)(6300000152)(1201174)(9300010160)(9300000332)(9301000404)(9305000129)(52401380)(52601095)(52505095)(52406095)(52305095)(52206115)(88860335)(82015058);SRVR:HE1EUR01HT023;BCL:0;PCL:0;RULEID:;SRVR:HE1EUR01HT023;

X-OriginatorOrg: outlook.com

X-MS-Exchange-CrossTenant-OriginalArrivalTime: 20 Feb 2019 10:57:53.0736

(UTC)

X-MS-Exchange-CrossTenant-Network-Message-Id: 9a8c2bf3-2724-4c67-c750-08d697224332

X-MS-Exchange-CrossTenant-Id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa

X-MS-Exchange-CrossTenant-FromEntityHeader: Internet

X-MS-Exchange-CrossTenant-RMS-PersistedConsumerOrg:

074d7d4d-72e2-4a0a-9d89-73b16535e4cd

X-MS-Exchange-Transport-CrossTenantHeadersStamped: HE1EUR01HT023

X-MS-Exchange-Transport-EndToEndLatency: 00:00:00.6181187

X-MS-Exchange-Processed-By-BccFoldering: 15.20.1622.000

X-Microsoft-Antispam-Mailbox-Delivery:

abwl:0;wl:0;pcwl:0;kl:0;iwl:0;dwl:0;dkl:0;rwl:0;ucf:0;jmr:0;ex:0;auth:1;dest:J;OFR:SpamFilterAuthJ;ENG5062000261)(5061607266)(5061608174)(4900095)(4920090)(6350004)(4950130)(4990090)(9140004);RF:JunkEmail;

X-Message-Info:

qoGN4b5S4yrIw3CxWeetTo8qsRQRMwd9vQDncbOz/epObqB0DARmbvQyuWeMO9RNHvKhxvdi9SRZTVI7xVDwil6l8bUUkaDvJhFDLqat4u+5XAM2NfrFGeFTSN9eQ/hEtkk0ZKpua6oq8yECHQ0pQVTNY9DsaLaJn6XvwEidbaYYlpoxQbzY9nqmGLfpSufTTFp8bVJa0yp/gRUZQLq39w==

X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02

X-Microsoft-Antispam-Message-Info:

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

MIME-Version: 1.0



Mensaje de prueba

Help me? Thanks!

 

[Mikhail Lapkin]

Judging from

X-Microsoft-Antispam-Mailbox-Delivery:

abwl:0;wl:0;pcwl:0;kl:0;iwl:0;dwl:0;dkl:0;rwl:0;ucf:0;jmr:0;ex:0;auth:1;dest:J;OFR:SpamFilterAuthJ;ENG:(5062000261)(5061607266)(5061608174)(4900095)(4920090)(6350004)(4950130)(4990090)(9140004);RF:JunkEmail;

it has to be Outlook issue so I'd suggest contact Outlook support. Although all SPF/DKIM seem to be fine Outlook still can apply its own message filtering rules and looks like they really do this.

 

[Kaspar]

So the mail you are sending from your VPS to any Hotmail/Outlook account ends up in the spam folder?

This is always tricky to trouble shoot. From the mail headers you posted it seems that SPF and DKIM are configured correctly. So it might be that your IP adres has a bad reputation at Microsoft. I guess the best thing would be to ask your VPS provider to help. Alternatively you cloud also use a mail relay to route your mail from an other server.

ps. This not a really Plesk related problem.

 

[tim-essen]

I found a solution for the case that the mails are forwarded to the Junk-Folder and the IP-address is not on a Microsoft-Blacklist.

3 Things are important:

1. SPF + DKIM are enabled.
2. You have to use a display name in all mail clients (Only imortant for the first mail sended to an outlook.com-mailbox)
3. You have to edit the postfix-configuration-file (/etc/postfix/main.cf)
Search for the line mydestination. You'll find a few entries (comma-separated).
Add your hostname to this list.
Restart Postfix: service postfix restart.

This worked for me.