Issue Problem Delivering Emails to Outlook/Hotmail Inbox (Ends up in Spam)

[ruleragency]

Hello,
I have been facing a problem with outlook/hotmail for many years with many different servers using plesk. All emails to outlook/hotmail addresses go to the spam folder at best.
I spent many hours searching the forum and setting up PTR records, SPF records but without any luck.

For example the domain especially.gr:
PTR Record in place for IPv4 & IPv6
SPF Record: v=spf1 +a +mx +a:especially.gr -all (also tried v=spf1 +a +mx +a:server.rulerhost.com -all)
DKIM Enabled

The IP is relevantly new, a few months of low use and not in any blacklist.

Can someone point me to the right direction to solve this issue?

Thanks!

Below you can find the header of an email send to an outlook address

Received: from AM6PR01MB4119.eurprd01.prod.exchangelabs.com

 (2603:10a6:20b:25::32) by AM6PR01MB6085.eurprd01.prod.exchangelabs.com with

 HTTPS; Tue, 1 Feb 2022 17:58:29 +0000

Received: from AS8PR07CA0034.eurprd07.prod.outlook.com (2603:10a6:20b:459::19)

 by AM6PR01MB4119.eurprd01.prod.exchangelabs.com (2603:10a6:20b:25::32) with

 Microsoft SMTP Server (version=TLS1_2,

 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.4930.20; Tue, 1 Feb

 2022 17:58:28 +0000

Received: from VI1EUR06FT019.eop-eur06.prod.protection.outlook.com

 (2603:10a6:20b:459:cafe::2c) by AS8PR07CA0034.outlook.office365.com

 (2603:10a6:20b:459::19) with Microsoft SMTP Server (version=TLS1_2,

 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.4951.10 via Frontend

 Transport; Tue, 1 Feb 2022 17:58:28 +0000

Authentication-Results: spf=pass (sender IP is 116.202.233.51)

 smtp.mailfrom=especially.gr; dkim=none (message not signed)

 header.d=none;dmarc=pass action=none header.from=especially.gr;compauth=pass

 reason=100

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

 116.202.233.51 as permitted sender) receiver=protection.outlook.com;

 client-ip=116.202.233.51; helo=especially.gr;

Received: from especially.gr (116.202.233.51) by

 VI1EUR06FT019.mail.protection.outlook.com (10.13.7.161) with Microsoft SMTP

 Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id

 15.20.4951.12 via Frontend Transport; Tue, 1 Feb 2022 17:58:28 +0000

X-IncomingTopHeaderMarker:

 OriginalChecksum:B04EBF81C11845B14066E0D553D59BC385672BB5039449C7CDD7F2941750BDB8;UpperCasedChecksum:A5368B9C903262DD4DEBB2D45A1DE13241BB5FAA991C6044EA799486602509B0;SizeAsReceived:1332;Count:21

Received: from DB9PR09MB5018.eurprd09.prod.outlook.com (unknown [IPv6:2603:1026:c02:408b::5])

    by server.rulerhost.com (Postfix) with ESMTPSA id 8B975214145C

    for <wehitch@outlook.com>; Tue,  1 Feb 2022 18:58:27 +0100 (CET)

Authentication-Results-Original: server.rulerhost.com;        spf=pass (sender

 IP is 2603:1026:c02:408b::5) smtp.mailfrom=estefanou@especially.gr

 smtp.helo=DB9PR09MB5018.eurprd09.prod.outlook.com

Received-SPF: pass (server.rulerhost.com: connection is authenticated)

From: "estefanou@especially.gr" <estefanou@especially.gr>

To: "wehitch@outlook.com" <wehitch@outlook.com>

Subject: =?iso-8859-7?B?yuHr5/Pw3fHh?=

Thread-Topic: =?iso-8859-7?B?yuHr5/Pw3fHh?=

Thread-Index: AQHYF5VFH6k9k7Oc4UOgVnApjd+PbQ==

X-MS-Exchange-MessageSentRepresentingType: 1

Date: Tue, 1 Feb 2022 17:58:24 +0000

Message-ID: <DB9PR09MB50185DAE7F0CD2D78183FB23F7269@DB9PR09MB5018.eurprd09.prod.outlook.com>

Accept-Language: en-US

Content-Language: en-GB

X-MS-Has-Attach:

X-MS-TNEF-Correlator:

Content-Type: multipart/alternative;

 boundary="_000_DB9PR09MB50185DAE7F0CD2D78183FB23F7269DB9PR09MB5018eurp_"

X-PPP-Message-ID: <164373830771.966114.14840634573119930207@server.rulerhost.com>

X-PPP-Vhost: especially.gr

X-IncomingHeaderCount: 21

Return-Path: estefanou@especially.gr

X-MS-Exchange-Organization-ExpirationStartTime: 01 Feb 2022 17:58:28.2530

 (UTC)

X-MS-Exchange-Organization-ExpirationStartTimeReason: OriginalSubmit

X-MS-Exchange-Organization-ExpirationInterval: 1:00:00:00.0000000

X-MS-Exchange-Organization-ExpirationIntervalReason: OriginalSubmit

X-MS-Exchange-Organization-Network-Message-Id:

 804dbc11-8613-44b4-5511-08d9e5ac7361

X-EOPAttributedMessage: 0

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

X-MS-Exchange-Organization-MessageDirectionality: Incoming

X-MS-PublicTrafficType: Email

X-MS-Exchange-Organization-AuthSource:

 VI1EUR06FT019.eop-eur06.prod.protection.outlook.com

X-MS-Exchange-Organization-AuthAs: Anonymous

X-MS-UserLastLogonTime: 2/1/2022 5:53:48 PM

X-MS-Office365-Filtering-Correlation-Id: 804dbc11-8613-44b4-5511-08d9e5ac7361

X-MS-TrafficTypeDiagnostic: AM6PR01MB4119:EE_

X-MS-Exchange-EOPDirect: true

X-Sender-IP: 116.202.233.51

X-SID-PRA: ESTEFANOU@ESPECIALLY.GR

X-SID-Result: PASS

X-MS-Exchange-Organization-PCL: 2

X-MS-Exchange-Organization-SCL: 5

X-Microsoft-Antispam: BCL:0;

X-MS-Exchange-CrossTenant-OriginalArrivalTime: 01 Feb 2022 17:58:28.2061

 (UTC)

X-MS-Exchange-CrossTenant-Network-Message-Id: 804dbc11-8613-44b4-5511-08d9e5ac7361

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

X-MS-Exchange-CrossTenant-AuthSource:

 VI1EUR06FT019.eop-eur06.prod.protection.outlook.com

X-MS-Exchange-CrossTenant-AuthAs: Anonymous

X-MS-Exchange-CrossTenant-FromEntityHeader: Internet

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

 00000000-0000-0000-0000-000000000000

X-MS-Exchange-Transport-CrossTenantHeadersStamped: AM6PR01MB4119

X-MS-Exchange-Transport-EndToEndLatency: 00:00:01.4846362

X-MS-Exchange-Processed-By-BccFoldering: 15.20.4930.022

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:(5062000285)(90000117)(90005022)(91005020)(91035115)(5061607266)(5061608174)(9050020)(9100338)(2008001134)(2008000189)(2008120399)(2008019284)(2008021020)(8390246)(4810002)(4910013)(9610025)(9560006)(10180021)(9320005)(9245025);RF:JunkEmail;

X-Message-Info:

    qoGN4b5S4yqyM3u8EmkEzxMi1pw0JtjyCMtFLdlrPbrMbPrJufCuuFLxomigF3XNRKd244ktj/VxQsQFDSdH2RfQQkMuD2ZwbcJcpijUxkais8KKSNtG0/Cz2ZPxhu25ljAiAeyFzDhVd7+uoQ7CX8Ln3IuD+togWN1s/XQARHG6AzDuBCFkVzRDH+iCHWRAALM9Ph5lV+hni2P3jLJwTw==

X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02

X-Microsoft-Antispam-Message-Info:

    =?iso-8859-7?Q?hCxSfCBKCJqgaD5yXg5J4mGR+eshmLtGWxOLLw1UnnDWSKF8l5s5FcAHW8?=

 =?iso-8859-7?Q?H/3wpTgiaYmRWmAsBORs7RsF8rIsZWVDDor0DfuP0EEcz/dO99YIeos50k?=

 =?iso-8859-7?Q?+XFIe0iRUBrYaZnqhyLS74RW/0UArz4S03rhbW5My0OIWjSge/4RXd987m?=

 =?iso-8859-7?Q?uUZxDZMui/xCtwoGJHqnSdJxFhrfH3/PNPqKVdJIgTHruSgc537PLAodl9?=

 =?iso-8859-7?Q?8z7kecmjtm6QM8nAt5ojAY+dUjD1FzmwPylezBAVXBHrMdfi5xLdfDPAbA?=

 =?iso-8859-7?Q?qsTyVTKi6bwwbf+Rx7ijD0wwo0RvJcezpjB8vdEa80iU95qjgBA5cgvdLF?=

 =?iso-8859-7?Q?UxY0xHoC1UDwxxhyBf9dEqOaNOm3ubvi49UlayciRCIkDRcR6HLdD2EolK?=

 =?iso-8859-7?Q?J00TaUeWUHeVDMWlt0QizSTSZNCppqS1xnfYWqYuB7w2OFu0TzvT8AbOul?=

 =?iso-8859-7?Q?aw9t/jgBivvhgueZhGG6KLt4Zs0nuJLneCB4FDkeeiyXKAdh3Xh8t82TBz?=

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 =?iso-8859-7?Q?y8gc3OTnsT8XbdACURqTqlqqYWNaw/VH00zIbgpdXaHlfqz+3h4r6kgy6V?=

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MIME-Version: 1.0



--_000_DB9PR09MB50185DAE7F0CD2D78183FB23F7269DB9PR09MB5018eurp_

Content-Type: text/plain; charset="iso-8859-7"

Content-Transfer-Encoding: quoted-printable



=D4=E9 =EA=DC=ED=E5=F4=E5?



--_000_DB9PR09MB50185DAE7F0CD2D78183FB23F7269DB9PR09MB5018eurp_

Content-Type: text/html; charset="iso-8859-7"

Content-Transfer-Encoding: quoted-printable

 

[mow]

You're setting

Content-Language: en-GB

but your content is encoded as

charset="iso-8859-7"

so you should configure your mailer to use gr-GR or something.

Additionally, the text/plain part of your mail is very short.
So maybe hotmail files your mail as spam because, you know, it looks like spam? Just saying.