Plesk email goes to Gmail spam and is rejected by outlook

Question

I created an instance on AWS Amazon an installed Plesk trial for a month

First problem that I discovered is that I coulnd't register my DNS on the plesk panel, cause I had just one IP and my domain provider (registro.br) requires 2 ips for dns (I know that Route53 is an option, but I have so many domains, it'd be expensive), so I had to duplicate all dns records generated by plesk to my registro.br dns manager

Second problem is that all my e-mails is going to spam on gmail and been rejected by outlook , I searched on the gmail headers message to find out why, first I solved an DKIM that wasn't passing, but now, SPF, DKIM and DMARC pass but it still with the same problem

Here is my gmail message header

Delivered-To: andreluismonteiro33@gmail.com
Received: by 2002:a5d:43cb:0:0:0:0:0 with SMTP id v11csp5983036wrr;
        Wed, 27 Mar 2019 04:35:17 -0700 (PDT)
X-Google-Smtp-Source: APXvYqzW3R3CzTzXlriAjBGdijdyPfwAG3wrCpYA0ZCMDWW/unHc0BcyC6cgpv207SK3aOu5rLYz
X-Received: by 2002:a37:7b02:: with SMTP id w2mr254415qkc.225.1553686516947;
        Wed, 27 Mar 2019 04:35:16 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1553686516; cv=none;
        d=google.com; s=arc-20160816;
        b=ewYQPERXxFgaiVzPRplhOFb8IOtrKS/E+YiLV4q07h/wNKMVZ2RTowMacTmSs9hxS2
         7K0tIavCxfCHJpGXbVKe7d20DHQPeO2X2RV763F3zoLdfmunK4xiEL2itH6n60VJBi10
         OPrM7g7v2p/boWL2gr29m20hxkOv2TYvYNLS27N4Bx3u0pmha4LwpmeLupOlVshQPlL1
         OrEFCYqa92s4goJSun31OuzKK18r4qivvHpk/9Ntln76mE9oAj/66Zti/9DULljXm9tQ
         bRs+QTgu7SqFc8qAQ/rZ80otgaIOmihI6K3Eh+UeeeRl//T33Y1udZXCtz3tc1b9RoeS
         mjTw==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
        h=user-agent:message-id:subject:to:from:date
         :content-transfer-encoding:mime-version:dkim-signature;
        bh=IZzGk5hdbwv1XsfTE2Dngp1hMDfBwbnO3RaSFfeDt+k=;
        b=VM37h+XoHJK20uNPocaVd4DkXTBDvFA2kSPWQbw0E9YVjKS12PcHLq4cbXaxj4zMsr
         ZHW5jlLFkdfAl/x66rY7u8NozQy3jNMXWxgL5fEs7i5PP4G20icV4r4Wy0Vkf4IFKINp
         0xN7ytoI2XnIyC6gKO1UAnqoAGjc/KYPfgdEmfYr8UBAHTwNXI4WmR4CJAkr8K1Q+i8Z
         dCq9ZcpqBND40dPavJ6+cw5+RuD04pTN/Py4OY1pUbTdNPQ4aSsBMrgijvjtgwc5p2Mj
         N9KYHo8a3bxruORfAhGXWuJa/uMRuJc8Drqd34i58YdXe0ws3551ZhXFAdIxB4K6gsAb
         2GAg==
ARC-Authentication-Results: i=1; mx.google.com;
       dkim=pass header.i=@naifersistemas.com.br header.s=default header.b=jZvGchWi;
       spf=pass (google.com: domain of contato@naifersistemas.com.br designates 3.209.102.205 as permitted sender) smtp.mailfrom=contato@naifersistemas.com.br;
       dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=naifersistemas.com.br
Return-Path: <contato@naifersistemas.com.br>
Received: from naifersistemas.com.br (ec2-3-209-102-205.compute-1.amazonaws.com. [3.209.102.205])
        by mx.google.com with ESMTPS id y27si3573136qth.174.2019.03.27.04.35.16
        for <andreluismonteiro33@gmail.com>
        (version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
        Wed, 27 Mar 2019 04:35:16 -0700 (PDT)
Received-SPF: pass (google.com: domain of contato@naifersistemas.com.br designates 3.209.102.205 as permitted sender) client-ip=3.209.102.205;
Authentication-Results: mx.google.com;
       dkim=pass header.i=@naifersistemas.com.br header.s=default header.b=jZvGchWi;
       spf=pass (google.com: domain of contato@naifersistemas.com.br designates 3.209.102.205 as permitted sender) smtp.mailfrom=contato@naifersistemas.com.br;
       dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=naifersistemas.com.br
Received: from webmail.naifersistemas.com.br (localhost.localdomain [IPv6:::1]) by naifersistemas.com.br (Postfix) with ESMTPSA id 8FECF8BFD0 for <andreluismonteiro33@gmail.com>; Wed, 27 Mar 2019 11:35:16 +0000 (UTC)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=naifersistemas.com.br; s=default; t=1553686516; bh=IZzGk5hdbwv1XsfTE2Dngp1hMDfBwbnO3RaSFfeDt+k=; l=7; h=From:To:Subject; b=jZvGchWishigWIDTPn07tRDJTCnWVyMo45TbK1VACsi2uqHNBhA38iJqKtQuxRKfG
     QFAdtdy25lJONMIMkmMjL8A29wjkUN2Cg7kjgpbm6UP5QNqVKGIJYwoxRNtb5vd3da
     Wi4M/PHk3P4vcjKKGfg4Cq1JPC/e4+6dLr0TqkZU=
MIME-Version: 1.0
Content-Type: text/plain; charset=US-ASCII; format=flowed
Content-Transfer-Encoding: 7bit
Date: Wed, 27 Mar 2019 08:35:16 -0300
From: "André Luis Monteiro" <contato@naifersistemas.com.br>
To: andreluismonteiro33@gmail.com
Subject: teste
Message-ID: <5b66270df1b5aebef561a898e2c8c4d3@naifersistemas.com.br>
X-Sender: contato@naifersistemas.com.br
User-Agent: Roundcube Webmail/1.3.6

teste

Here is my outlook reject message

This is the mail system at host naifersistemas.com.br.

I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.

For further assistance, please send mail to postmaster.

If you do so, please include this problem report. You can
delete your own text from the attached returned message.

                   The mail system

<andre_luis_monteiro1998@hotmail.com>: host
    hotmail-com.olc.protection.outlook.com[104.47.46.33] said: 550 5.7.1
    Unfortunately, messages from [3.209.102.205] weren't sent. Please contact
    your Internet service provider since part of their network is on our block
    list (S3140). You can also refer your provider to
    http://mail.live.com/mail/troubleshooting.aspx#errors.
    [BN3NAM04FT044.eop-NAM04.prod.protection.outlook.com] (in reply to MAIL
    FROM command)
Reporting-MTA: dns; naifersistemas.com.br
X-Postfix-Queue-ID: 8FC9A8BFD1
X-Postfix-Sender: rfc822; contato@naifersistemas.com.br
Arrival-Date: Wed, 27 Mar 2019 11:33:09 +0000 (UTC)

Final-Recipient: rfc822; andre_luis_monteiro1998@hotmail.com
Original-Recipient: rfc822;andre_luis_monteiro1998@hotmail.com
Action: failed
Status: 5.7.1
Remote-MTA: dns; hotmail-com.olc.protection.outlook.com
Diagnostic-Code: smtp; 550 5.7.1 Unfortunately, messages from [3.209.102.205]
    weren't sent. Please contact your Internet service provider since part of
    their network is on our block list (S3140). You can also refer your
    provider to http://mail.live.com/mail/troubleshooting.aspx#errors.
    [BN3NAM04FT044.eop-NAM04.prod.protection.outlook.com]
Assunto teste
De  André Luis Monteiro
Para    andre_luis_monteiro1998@hotmail.com
Data    Hoje 08:33
teste

Answer 1

You can try couple of more thing: 1.Publish PTR for 3.209.102.205 to naifersistemas.com.br (or the value you're sending in EHLO) instead of ec2-3-209-102-205.compute-1.amazonaws.com.

Since this IP belongs to an Ec2 instance, Outlook may have blacklisted this (It does stupid things until you build the reputation). https://support.microsoft.com/en-us/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75 You can see if you can whitelist the IP using above link.

With Gmail, try to add some good message body and test it again , you can use this to check the score: https://www.mail-tester.com/