How do I fix email is caught as spam from Postfix

I have setup a local server with a postfix mail server using SPF and DKIM as well as reverse DNS lookup. Regardless my email is getting caught as spam on the MS Exchange Server. Here is my email source:

Received: from SN6PR04MB3965.namprd04.prod.outlook.com (2603:10b6:805:ca::33)
by SN6PR04MB3967.namprd04.prod.outlook.com with HTTPS via
SN6PR16CA0056.NAMPRD16.PROD.OUTLOOK.COM; Fri, 5 Apr 2019 13:33:59 +0000
Received: from DM5PR04CA0045.namprd04.prod.outlook.com (2603:10b6:3:12b::31)
by SN6PR04MB3965.namprd04.prod.outlook.com (2603:10b6:805:45::18) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.1750.17; Fri, 5 Apr
2019 13:33:56 +0000
Received: from DM3NAM03FT064.eop-NAM03.prod.protection.outlook.com
(2a01:111:f400:7e49::204) by DM5PR04CA0045.outlook.office365.com
(2603:10b6:3:12b::31) with Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384) id 15.20.1771.16 via Frontend
Transport; Fri, 5 Apr 2019 13:33:56 +0000
Authentication-Results: spf=pass (sender IP is 45.56.110.221)
smtp.mailfrom=oh-joy.org; toolingu.com; dkim=pass (signature was verified)
header.d=oh-joy.org;toolingu.com; dmarc=bestguesspass action=none
header.from=oh-joy.org;compauth=pass reason=109
Received-SPF: Pass (protection.outlook.com: domain of oh-joy.org designates
45.56.110.221 as permitted sender) receiver=protection.outlook.com;
client-ip=45.56.110.221; helo=oh-joy.org;
Received: from oh-joy.org (45.56.110.221) by
DM3NAM03FT064.mail.protection.outlook.com (10.152.83.1) with Microsoft SMTP
Server id 15.20.1750.16 via Frontend Transport; Fri, 5 Apr 2019 13:33:55
+0000
Received: by oh-joy.org (Postfix, from userid 0)
id 9D2BD43614; Fri, 5 Apr 2019 09:33:54 -0400 (EDT)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=oh-joy.org; s=201904;
t=1554471234; bh=Yx7w3w7Dyv1yjmuph1OA7KJWm7py7MidN5el3iL46c4=;
h=Subject:From:To:Date:From;
b=QUPjWscOk24copRcbJVnYzVgqA1pDyINUyClYRLgbGQ2jNTzTto8B+jIJTZcmQ2rO
u5EoRKw18OCkmmwPtV8Eu0T7yeF8YjPY5iOewy7aEC19jsBelITzmsxmEpHCoAoe5u
CLsvVCAaORN49w4IFEqRzosIfd/mF/YsbPP28ePJkqTBmt2GiszhA7/LRyyyHjMBTy
iacNOLiWKhZU2yOskMPJiALn5ZFqI40J0lxmqK+/H2aHq2VFvDKcT0zdi04xYHhel8
KrReRd5RlFGUtbdvf6edrmtMr38DiD9At0vy3diyRCKG4GEwxeqydcttDL+CZccLci
ykBGBCsdqKwtQ==
Subject: Working on test
From: OhJoy brad@oh-joy.org
To: brad.rice@toolingu.com
X-Mailer: mail (GNU Mailutils 3.4)
Message-ID: 20190405133354.9D2BD43614@oh-joy.org
Date: Fri, 5 Apr 2019 09:33:54 -0400 (EDT)
Return-Path: brad@oh-joy.org
X-MS-Exchange-Organization-ExpirationStartTime: 05 Apr 2019 13:33:55.3865
(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:
ef36daba-f112-4f81-5e31-08d6b9cb59b2
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: e4feb827-1196-496c-9b39-91cf263bffbf:0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
X-Forefront-Antispam-Report:
CIP:45.56.110.221;IPV:NLI;CTRY:;EFV:NLI;SFV:SPM;SFS:(189003)(199004)(90896003)(22186003)(126002)(1096003)(1076003)(36756003)(43003)(36906005)(6916009)(97876018)(118176002)(16586007)(33656002)(48376002)(103686004)(486006)(42186006)(2160300002)(90966002)(104016004)(70486001)(40036005)(2616005)(7116003)(26005)(106466001)(81156014)(47776003)(558084003)(4270600006)(3480700005)(50226002)(106002)(305945005)(8266002)(2351001)(19618925003)(8676002)(34756004)(356004)(86362001)(58800400003)(69596002)(6266002)(476003)(336012)(51416003)(81166006)(426003)(620700002)(50466002)(5660300002)(61010400012)(12820200003);DIR:INB;SFP:;SCL:5;SRVR:SN6PR04MB3965;H:oh-joy.org;FPR:;SPF:Pass;LANG:en;PTR:li912-221.members.linode.com;MX:1;A:3;CAT:SPM;
MIME-Version: 1.0
X-MS-Exchange-Organization-AuthSource:
DM3NAM03FT064.eop-NAM03.prod.protection.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-PublicTrafficType: Email
X-MS-Office365-Filtering-Correlation-Id: ef36daba-f112-4f81-5e31-08d6b9cb59b2
X-Microsoft-Antispam:
BCL:0;PCL:0;RULEID:(2390118)(7020095)(4652040)(5600139)(711020)(4605104)(4709054)(1401320)(8001031)(1421009)(1414054)(71702078);SRVR:SN6PR04MB3965;
X-MS-TrafficTypeDiagnostic: SN6PR04MB3965:
X-MS-Exchange-Organization-SCL: 5
X-FOSE-spam: This message appears to be spam.
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 05 Apr 2019 13:33:55.2654
(UTC)
X-MS-Exchange-CrossTenant-Network-Message-Id: ef36daba-f112-4f81-5e31-08d6b9cb59b2
X-MS-Exchange-CrossTenant-Id: e4feb827-1196-496c-9b39-91cf263bffbf
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: SN6PR04MB3965
X-MS-Exchange-Transport-EndToEndLatency: 00:00:04.1242286
X-MS-Exchange-Processed-By-BccFoldering: 15.20.1771.000
X-Microsoft-Antispam-Mailbox-Delivery:
ucf:0;jmr:1;ex:0;auth:0;dest:J;ENG:(20160513016)(750119)(520011016)(944506303)(944626516);
X-Microsoft-Antispam-Message-Info:
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=?us-ascii?Q?8ACeDRCAhTEynB4LaGBhFfq78BMbiunRgKVGppFAxM65+lSlJNxEIBQSRMK6?=
=?us-ascii?Q?nBNoZnYr5ucqfK+lYTWG203fh7vcEMuYOv2UWRtT2Vg0ZYi4Bm/UHpRu3wzg?=
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=?us-ascii?Q?pIbszbTBJwUOxPosfNC9rYjuXRzWOh/lUR0KPHfoyLFsBdzSr6qqPxQrB/b/?=
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=?us-ascii?Q?dO2LQu7Lgb2jab8qa5szeTmBriTMiT/CjUP86QuqP5DupfDOzYUz/szYM9+O?=
=?us-ascii?Q?xko96Zei7sxPR/OC14AqSRvOTscKSXHoX/0SX0+6jlmvdulsCpRs7l44o6D2?=
=?us-ascii?Q?LsQt8J9b2JBxbhbb3ZG2qVpOURaKRWuykw9XACGV8XxZ5dYq2nnYeyIkBovk?=
=?us-ascii?Q?NqRrBF7wkhTJjg6CtcEHUcAt8vPKBtjplMSAkbI+qjzFnWdxtLKY14xRXczw?=
=?us-ascii?Q?W/xaVrxjA+SFKfCBip6OKcF4jNmpfSGWooAMC0Kalxd+JBamTTYbDVp+hpKo?=
=?us-ascii?Q?hoHRPirt9p4RqmLs0ma64qX+7YphJfVaVch+pSTeZpcjWrUkEfFdQnphHNub?=
=?us-ascii?Q?5FWT5S88tB5foL4Z72xhspNv4ZJsb462cOfyNcTE3r+fLXBNF3281RtxIy+X?=
=?us-ascii?Q?6CePqn6BghCnm9kySSa9jfCwjTw9MkQJlKooZQhB3D7dqNnxgATK+SVG8mDh?=
=?us-ascii?Q?Qp6v2ikiMeeuVHkoov47urglVcGVWoZ4q9dO+eF353HQOS1829mU6BUYb0la?=
=?us-ascii?Q?c0WF0roM0Gr2nNo/PcW3IYe/35Q5QHklgEppJ+n6P9RjiplogsS61Ide1AWu?=
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Content-type: text/plain;
charset="UTF-8"
Content-transfer-encoding: 7bit

This is from my new rivendell server

1 Reply

Email deliverability issues are a bit hard to diagnose. I can see that you have configured rDNS on your IP address, as well as SPF and DKIM records on your domain. I recommend double checking all of these settings and making sure they are valid. There's quite a number of tools online that might assist you in testing this.

Using mxtoolbox, I've also verified that your IP address and domain do not appear on any blacklists.

If you are sending bulk mail, you'll also want to implement a confirmed opt-in (double opt-in) signup process and include clear unsubscribe links in your messages.

It's important to know that your reputation as a sender should improve over time, provided that you are following best practices and not sending spam. Here's a few links that may be helpful to you:

Bulk sending guidelines: https://support.google.com/mail/answer/81126
Postmaster Tools: https://support.google.com/mail/answer/6227174

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