Email (Zimbra) server being marked as spam on gmail, yahoo, outlook, etc

February 28, 2016 10.9k views
Email Ubuntu
adamdistefano
By:
adamdistefano

Hi!

I've recently set up a Droplet with Ubuntu 14.04 and Zimbra for an educational experience.

Everything appears to be functional, but mail sent from my server is being marked as spam in gmail, yahoo, outlook, zoho. It doesn't even arrive on my fastmail address.

I'm pretty sure I've setup DKIM, SPF, DMARC correctly. The IP is not blacklisted.

SPF: 

v=spf1 a mx ~all

DKIM:

v=DKIM1; k=rsa; p=MIGfMA0GCSqGSIb3DQEBAQUAA4GNADCBiQKBgQC3PGJuQDhPZs0dcXz+8XbYO+qzL4E1FSXnOkU5G7JtP7wwE3hXwO4QxUgwhSGC8Z75naF57ewcN5brz7Pe1dqM3JXcEo71+bz6rjvXXO2RqU5jcY1gE2+XnHqUQo8A80YmosI9sgnIM7riFnjeyVB/jozxVDH3rPyhLLJ4T2PWLQIDAQAB

DMARC:

v=DMARC1; p=none; sp=none; rua=mailto:overseer@adamdistefanotesting.net; ruf=mailto:overseer@adamdistefanotesting.net; rf=afrf; pct=100; ri=86400

I've done some tests from

and they've come back all good.

This is the header from gmail.com

Delivered-To: adadington@gmail.com
Received: by 10.79.114.148 with SMTP id x20csp679347ivf;
        Sun, 28 Feb 2016 13:29:21 -0800 (PST)
X-Received: by 10.28.95.86 with SMTP id t83mr4161471wmb.86.1456694960924;
        Sun, 28 Feb 2016 13:29:20 -0800 (PST)
Return-Path: <me@adamdistefanotesting.net>
Received: from mail.adamdistefanotesting.net (mail.adamdistefanotesting.net. [188.166.149.143])
        by mx.google.com with ESMTPS id o65si16852275wmg.41.2016.02.28.13.29.20
        for <adadington@gmail.com>
        (version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
        Sun, 28 Feb 2016 13:29:20 -0800 (PST)
Received-SPF: pass (google.com: domain of me@adamdistefanotesting.net designates 188.166.149.143 as permitted sender) client-ip=188.166.149.143;
Authentication-Results: mx.google.com;
       spf=pass (google.com: domain of me@adamdistefanotesting.net designates 188.166.149.143 as permitted sender) smtp.mailfrom=me@adamdistefanotesting.net;
       dkim=pass header.i=@adamdistefanotesting.net;
       dmarc=pass (p=NONE dis=NONE) header.from=adamdistefanotesting.net
Received: from localhost (localhost [127.0.0.1])
    by mail.adamdistefanotesting.net (Postfix) with ESMTP id 8AB06163C0E
    for <adadington@gmail.com>; Sun, 28 Feb 2016 16:29:20 -0500 (EST)
Received: from mail.adamdistefanotesting.net ([127.0.0.1])
    by localhost (mail.adamdistefanotesting.net [127.0.0.1]) (amavisd-new, port 10032)
    with ESMTP id vU_psJQzD0gz for <adadington@gmail.com>;
    Sun, 28 Feb 2016 16:29:20 -0500 (EST)
Received: from localhost (localhost [127.0.0.1])
    by mail.adamdistefanotesting.net (Postfix) with ESMTP id 46F76163C0F
    for <adadington@gmail.com>; Sun, 28 Feb 2016 16:29:20 -0500 (EST)
DKIM-Filter: OpenDKIM Filter v2.9.2 mail.adamdistefanotesting.net 46F76163C0F
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
    d=adamdistefanotesting.net; s=63D45294-DD71-11E5-80CD-EC072571FB25;
    t=1456694960; bh=9dMgoyW9RC1ErB1b7m61zvVeWcMF/6UmzbLMDlsy4yw=;
    h=To:From:Subject:Message-ID:Date:MIME-Version:Content-Type:
     Content-Transfer-Encoding;
    b=AoxReKW2IU8o0lr1Y5JD3syTPcZ48y9UNGwHD62qycuInzU3m8Cc/JlGD0l/c5+hJ
     FC3UfTPgo2sBzQImdfgzvvtvGpKbm9Cw/vAqaJvBt5mApSBl9s9FLjKSPzZQWKGgqO
     c0Yckks0WSWKdnR9J95gdHjVo23EQE87bP5CdBs0=
X-Virus-Scanned: amavisd-new at adamdistefanotesting.net
Received: from mail.adamdistefanotesting.net ([127.0.0.1])
    by localhost (mail.adamdistefanotesting.net [127.0.0.1]) (amavisd-new, port 10026)
    with ESMTP id 70gm_rSWAKNE for <adadington@gmail.com>;
    Sun, 28 Feb 2016 16:29:20 -0500 (EST)
Received: from Adams-MBP.home ([redacted]])
    by mail.adamdistefanotesting.net (Postfix) with ESMTPSA id 232FC163C0E
    for <adadington@gmail.com>; Sun, 28 Feb 2016 16:29:20 -0500 (EST)
To: adadington@gmail.com
From: Adam Distefano <me@adamdistefanotesting.net>
Subject: Hello Adam!
Message-ID: <56D366AF.4070109@adamdistefanotesting.net>
Date: Sun, 28 Feb 2016 21:29:19 +0000
User-Agent: Mozilla/5.0 (Macintosh; Intel Mac OS X 10.10; rv:38.0)
 Gecko/20100101 Thunderbird/38.6.0
MIME-Version: 1.0
Content-Type: text/plain; charset=utf-8; format=flowed
Content-Transfer-Encoding: 7bit

This is the header from outlook.com

Received: from HE1PR07MB1705.eurprd07.prod.outlook.com (10.166.124.147) by
 AM4PR07MB1697.eurprd07.prod.outlook.com (10.166.133.17) with Microsoft SMTP
 Server (TLS) id 15.1.415.20 via Mailbox Transport; Sun, 28 Feb 2016 21:41:56
 +0000
Received: from AM2PR07CA0037.eurprd07.prod.outlook.com (10.163.24.175) by
 HE1PR07MB1705.eurprd07.prod.outlook.com (10.166.124.147) with Microsoft SMTP
 Server (TLS) id 15.1.415.20; Sun, 28 Feb 2016 21:41:56 +0000
Received: from DB5EUR01FT054.eop-EUR01.prod.protection.outlook.com
 (2a01:111:f400:7e02::204) by AM2PR07CA0037.outlook.office365.com
 (2a01:111:e400:8448::47) with Microsoft SMTP Server (TLS) id 15.1.415.20 via
 Frontend Transport; Sun, 28 Feb 2016 21:41:55 +0000
Received: from BAY004-MC3F51.hotmail.com (10.152.4.54) by
 DB5EUR01FT054.mail.protection.outlook.com (10.152.5.133) with Microsoft SMTP
 Server (TLS) id 15.1.422.5 via Frontend Transport; Sun, 28 Feb 2016 21:41:54
 +0000
Received: from mail.adamdistefanotesting.net ([188.166.149.143]) by BAY004-MC3F51.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23143);
     Sun, 28 Feb 2016 13:41:53 -0800
Received: from localhost (localhost [127.0.0.1])
    by mail.adamdistefanotesting.net (Postfix) with ESMTP id B7042163C10
    for <adamdistefanospamtest@outlook.com>; Sun, 28 Feb 2016 16:41:51 -0500 (EST)
Received: from mail.adamdistefanotesting.net ([127.0.0.1])
    by localhost (mail.adamdistefanotesting.net [127.0.0.1]) (amavisd-new, port 10032)
    with ESMTP id DQkKUy0tKrBt for <adamdistefanospamtest@outlook.com>;
    Sun, 28 Feb 2016 16:41:51 -0500 (EST)
Received: from localhost (localhost [127.0.0.1])
    by mail.adamdistefanotesting.net (Postfix) with ESMTP id 75A98163C11
    for <adamdistefanospamtest@outlook.com>; Sun, 28 Feb 2016 16:41:51 -0500 (EST)
DKIM-Filter: OpenDKIM Filter v2.9.2 mail.adamdistefanotesting.net 75A98163C11
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
    d=adamdistefanotesting.net; s=63D45294-DD71-11E5-80CD-EC072571FB25;
    t=1456695711; bh=cAGOiJ16wt7hb4RdFkkeaSsytzz3mwQBVtcQPZ6U93s=;
    h=To:From:Subject:Message-ID:Date:MIME-Version:Content-Type:
     Content-Transfer-Encoding;
    b=WIRfh/iyPOmtmDk8c4i4E9kCwLZOPlCKK7s7OGOYnTlAsfOqmkENtwFoLe5N+KExE
     4UEeDpQg0dYvYOwON7ucVOC0VXnbkrGwPNqCgYDi6FBCbeDdjIEicpVB0tTA8Y9bS9
     e8jqDzArqL42OxiMqKlq+Ugup+JZeK9B9Ka52v0A=
X-Virus-Scanned: amavisd-new at adamdistefanotesting.net
Received: from mail.adamdistefanotesting.net ([127.0.0.1])
    by localhost (mail.adamdistefanotesting.net [127.0.0.1]) (amavisd-new, port 10026)
    with ESMTP id nLYzJUoYl5Fy for <adamdistefanospamtest@outlook.com>;
    Sun, 28 Feb 2016 16:41:51 -0500 (EST)
Received: from Adams-MBP.home ([redacted])
    by mail.adamdistefanotesting.net (Postfix) with ESMTPSA id 529E1163C10
    for <adamdistefanospamtest@outlook.com>; Sun, 28 Feb 2016 16:41:51 -0500 (EST)
To: adamdistefanospamtest@outlook.com
From: Adam Distefano <me@adamdistefanotesting.net>
Subject: Hello outlook.com!
Message-ID: <56D3699E.1000306@adamdistefanotesting.net>
Date: Sun, 28 Feb 2016 21:41:50 +0000
User-Agent: Mozilla/5.0 (Macintosh; Intel Mac OS X 10.10; rv:38.0)
 Gecko/20100101 Thunderbird/38.6.0
Content-Type: text/plain; charset=utf-8; format=flowed
Content-Transfer-Encoding: 7bit
Return-Path: me@adamdistefanotesting.net
X-OriginalArrivalTime: 28 Feb 2016 21:41:53.0669 (UTC) FILETIME=[D6D5BB50:01D17270]
X-MS-Exchange-Organization-Network-Message-Id: 225c6098-8770-479c-1152-08d34087fa8f
X-EOPAttributedMessage: 0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
CMM-sender-ip: 188.166.149.143
CMM-sending-ip: 188.166.149.143
CMM-Authentication-Results: hotmail.com; spf=pass (sender IP is
 188.166.149.143; identity alignment result is pass and alignment mode is
 relaxed) smtp.mailfrom=me@adamdistefanotesting.net; dkim=pass (identity
 alignment result is pass and alignment mode is relaxed)
 header.d=adamdistefanotesting.net; x-hmca=pass
 header.id=me@adamdistefanotesting.net
CMM-X-SID-PRA: me@adamdistefanotesting.net
CMM-X-AUTH-Result: PASS
CMM-X-SID-Result: PASS
CMM-X-Message-Status: n:n
CMM-X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
CMM-X-Message-Info: 11chDOWqoTlIU1CdRjWHQ35Q/eFtyU8Fdnzvt7eh7gtzZlPuvccoGHp4O6yeXlNxNs1p6Qs0fpY9mOw8aC8vXVlpGzZ9IoKuuGDcs/2FwTarhqsVvYoYad0oLf/+EJfFXbYl31/loSEM13THP8El2M1EdxuqduoPaCilU1q12xTQpEKsrN00/wHSSbOqNfAtJVip0yP274md4vsihbh73KbIeHDvy9I1q3VJQL7h9sY=
X-MS-Exchange-Organization-SCL: 6
X-MS-Exchange-Organization-PCL: 2
X-Forefront-Antispam-Report: CIP:25.152.4.54;CTRY:GB;IPV:NLI;EFV:NLI;SFV:SKS;SFS:;DIR:INB;SFP:;SCL:6;SRVR:HE1PR07MB1705;H:BAY004-MC3F51.hotmail.com;FPR:;SPF:None;LANG:en;
X-Microsoft-Exchange-Diagnostics: 1;HE1PR07MB1705;2:elhWz2xFCOm5S5xkewqyMN7Aekg5XTTQ5CxyNXAhAH1cKj3w8OByX32cOOfuREnQgkc7DwpnCaeOgdvQY97wCmEchrwCPzpjfxIMUAD/Zv1D2ynjH8FVw0pDPVenCuQSt98DWarvmRGlRojyA6b18dsNdprjqVSAC2v0iYq3Z/akkc5r6Ys5V879k563ihc/;3:F9ztUMkXf0At4sx8i1BEYNxZvyGfSCT/cdce5Iy5hvHfAQO6X3tdOXI8At+nu4w8ajZCSm9NznOmiT6sJ8LSGIjumXn2GAz8TPNAcVxFLd56T93B3WIfI1PJ+VsXFKBy43NzEXJc1K+pcu+zEMVXK2gC2Zqmsjbon00csf4hzNUA1ExM6fBE/EGrGNoupff5w5ZsAk4ajcS8HEZtDFCd7Q==;25:MlvNamFLuCjWNM7r+/2FwqiDc/XgEXBBAdqYQ7bFq+ctW6Yg5nEhUhYA2SXOMrAhNnYBQVTs6YTM106lf9cLIUvsh6U3nw8HY5tLT33TtZoMgdUQmkkTW4b0NRS7BC//ZDxeAHlpCL/GjrZCwBVaOBmrcW9NOMmsUXLubSbcfWBKXFAh9ir2UFYGjuBWqtD8Csb7Zy/dWqHuubQ0PWpuV3e7BKAVhQyPtJH1gP5R6zi8tmLh7BRM9NA0DIktTn4Aw+E/KNj0nNeuxbAxbEopt8Iqn13l2Dk6Q0G+KRmFcmidw7SbZWT/aLamWo2I5IAG
X-Microsoft-Antispam: BCL:0;PCL:0;RULEID:(8291501001);SRVR:HE1PR07MB1705;
X-MS-Office365-Filtering-Correlation-Id: 225c6098-8770-479c-1152-08d34087fa8f
X-MS-Exchange-Organization-AVStamp-Service: 1.0
X-Exchange-Antispam-Report-CFA-Test: BCL:0;PCL:0;RULEID:(82015046);SRVR:HE1PR07MB1705;BCL:0;PCL:0;RULEID:;SRVR:HE1PR07MB1705;
X-Microsoft-Exchange-Diagnostics: 1;HE1PR07MB1705;4:hRBwhRBGqAMiCY/slt6F1ecPe5bSaVeZznxwZxTY2hlJLT1sIO28io7HldfCNQ6HGnfLxqBuzQrZBd0gx1FTYfHajI2HQ1DhlymU4e5TSDfWaUanyAVIqC/VHB/EB80xdCEqcBwFjbYAEB+b04Qv5sTG0Pds714gTJmYN73QLKatszyh9B7guKEvL70TbG05V0I9Srjbj4Gzt5OcLfMXWNWrluvSiaqc6s+6Px+hCNCl4NZAAeLQ3Ia6zbLUbHpQ9qoBbZJXixjOcKD90p+/EQ==;23:ouma+JQsYygiaex9wCHoyRz8w+mqoE8Z1d1UtZohi2nAL1y+jIjoxlfOjF26ggq/j/eOnYKu1l1+IHZR1RFUU6yE1WPeJHPGVNeYJKgMQfm1+4ujdTNs9mYS9J8ded+akmxiyj3ngcNScO3rPDxoJxIPUlI2+H+xkDLqOKjFQGCX5wY0bEqprz7ZuqKUB8VO;5:1gyM1iGP7bs4KEG2zL89oJiE6orq92Z6DmjFMAIxtjs2zgkEnL3kOnrd2OxU28+MJL75iawRHQa4Dm9hBf1bwpMRR+RU/lN9pMlL/NcLs0wWnsYDhBjKvvN2S9TYytuFCUnKlHxolTHPRxvZsejUbg==;24:i5VgqKjV6ZA+mvL7PD80hq+St60YqwQtyyOHVEXNYQwz1DtN4mWC1lfyh4RRkR8bhsdplEa8zwBhCBs4LCEuhw==
SpamDiagnosticOutput: 1:23
SpamDiagnosticMetadata: SKS
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 28 Feb 2016 21:41:54.7970
 (UTC)
X-MS-Exchange-CrossTenant-Id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: HE1PR07MB1705
X-MS-Exchange-Organization-AuthSource: DB5EUR01FT054.eop-EUR01.prod.protection.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-Exchange-Transport-EndToEndLatency: 00:00:02.1601887
MIME-Version: 1.0

I really have no idea why my mail is being marked. The headers state that dmarc, dkim and spf are passing.

Any help would be apprecaited!

Cheers

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1 Answer
mragusa March 9, 2016

Hello,

While it's great to hear that SPF, DKIM , and DMARC are setup correctly, they are mainly used as anti-spoofing mechanisms and are not used to guarantee delivery despite how people advertise the technology.

Many mail systems used IP reputation and complicated algorithms to determine if an email message is spam or not. A good place to check your reputation is here: https://www.senderbase.org/lookup/?search_string=188.166.149.143

You may want to apply for whitelist status with the various ESPs to ensure your domain is not caught up with any further issues.

Please let us know if there is anything else we can help you with.

Best,
Mike
DigitalOcean Support
Check out our community for great tutorials, articles and FAQs!
https://digitalocean.com/community

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