Postfix sends email to spam (gmail, hotmail)

razorxan asked:

I recently installed a postfix + dovecot + dkim multi domain, multi user, multi alias mail server on my debian squeeze system. Everything works except for one big issue that basically makes the whole thing useless:

Every single email sent by my server goes straight into spam. (gmail, hotmail)

First thing i did is doing the well known allaboutspam test and all is checked (green) except for the BATV thing (yellow):

Reverse dns: green
HELO Greeting: green
RBL: green
BATV: yellow
SPF: green
DKIM: green
URIBL: green
SPAMAssassin: green
Greylist: green

I’m really confused and i can’t see a way to solve this issue.
Ask me any detail if you need.

EDIT:

Headers example http://pastebin.com/zdcBciXQ

EDIT

mail-tester gives me 9.9 out of 10 as score. source of the email sent to mail-tester

Received: by mail-tester.com (Postfix, from userid 500) id 9FF4F1C8268;
    Mon,  9 Jun 2014 15:31:28 +0200 (CEST)
X-Spam-Checker-Version: SpamAssassin 3.3.2 (2011-06-06) on mail-tester.com
X-Spam-Level: 
X-Spam-Status: No/0.1/5.0
X-Spam-Test-Scores: BODY_URI_ONLY=0.249,DKIM_SIGNED=0.1,DKIM_VALID=-0.1,
    DKIM_VALID_AU=-0.1,SPF_PASS=-0.001
X-Spam-Last-External-IP: 46.252.151.58
X-Spam-Last-External-HELO: vps-0220.flarevm.net
X-Spam-Last-External-RDNS: vps-0220.flarevm.net
X-Spam-Date-of-Scan: Mon, 09 Jun 2014 15:31:28 +0200
Received: from vps-0220.flarevm.net (vps-0220.flarevm.net [46.252.151.58])
    by mail-tester.com (Postfix) with ESMTP id 95C491C80AF
    for <web-p5be8g@mail-tester.com>; Mon,  9 Jun 2014 15:31:23 +0200 (CEST)
Received: from [192.168.0.196] (93-58-82-129.ip157.fastwebnet.it [93.58.82.129])
    by vps-0220.flarevm.net (Postfix) with ESMTPA id 831B2882AC
    for <web-p5be8g@mail-tester.com>; Mon,  9 Jun 2014 15:34:10 +0200 (CEST)
X-DKIM: Sendmail DKIM Filter v2.8.2 vps-0220.flarevm.net 831B2882AC
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=totoamici.club;
    s=default; t=1402320850;
    bh=g3zLYH4xKxcPrHOD18z9YfpQcnk/GaJedfustWU5uGs=;
    h=Message-ID:Date:From:MIME-Version:To:Subject:Content-Type:
    Content-Transfer-Encoding;
    b=m3VcrhgRe9qg1UYV/vaewCtjLkon0smrnVjViRaqXeWlyVPdJMRhqCrBPwucE3Ha/
    ubXTB2vcS3Fzje70WWnOWudL3hWNAVDVUissoTBPM+DdWronyqyFJKbX4IDMPahbW4
    i5Ib+f5SUqI5rpj48xIn/2Bz/fKXBj6ZCElH9Pis=
Message-ID: <5395B7D3.9090704@totoamici.club>
Date: Mon, 09 Jun 2014 15:34:11 +0200
From: Info Totoamici <info@totoamici.club>
User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64; rv:24.0) Gecko/20100101
    Thunderbird/24.5.0
To: web-p5be8g@mail-tester.com
Subject: test
Return-Path: info@totoamici.club
MIME-Version: 1.0
Content-Type: text/plain; charset=ISO-8859-15; format=flowed
Content-Transfer-Encoding: 7bit

test

EDIT

gmail mail (seen as spam)
gmail says:

"Why is this message in Spam? It's similar to messages that have been detected by our spam filters."

source:

Delivered-To: mypersonal@gmail.com
Received: by 10.194.34.72 with SMTP id x8csp126077wji;
        Mon, 9 Jun 2014 07:21:56 -0700 (PDT)
X-Received: by 10.195.12.34 with SMTP id en2mr32657473wjd.13.1402323716664;
        Mon, 09 Jun 2014 07:21:56 -0700 (PDT)
Return-Path: <info@internest.it>
Received: from vps-0220.flarevm.net (vps-0220.flarevm.net. [46.252.151.58])
        by mx.google.com with ESMTP id j10si6131780wjq.139.2014.06.09.07.21.55
        for <mypersonal@gmail.com>;
        Mon, 09 Jun 2014 07:21:55 -0700 (PDT)
Received-SPF: pass (google.com: domain of info@internest.it designates 46.252.151.58 as permitted sender) client-ip=46.252.151.58;
Authentication-Results: mx.google.com;
       spf=pass (google.com: domain of info@internest.it designates 46.252.151.58 as permitted sender) smtp.mail=info@internest.it;
       dkim=pass header.i=@internest.it
Received: from [192.168.0.196] (93-58-82-129.ip157.fastwebnet.it [93.58.82.129])
    by vps-0220.flarevm.net (Postfix) with ESMTPSA id B4E6A882AC
    for <mypersonal@gmail.com>; Mon,  9 Jun 2014 16:21:52 +0200 (CEST)
X-DKIM: Sendmail DKIM Filter v2.8.2 vps-0220.flarevm.net B4E6A882AC
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=internest.it;
    s=default; t=1402323712;
    bh=ttxTWNNYqcgPkN0JdFCDc/piQyq9inHM1Fn12webR1c=;
    h=Message-ID:Date:From:MIME-Version:To:Subject:Content-Type:
     Content-Transfer-Encoding;
    b=K4pFsf81nTgF5iMN4gMMDmy7+Seci/fWUYOpr/bjA2weYYzOCq73J3Qs3nIyshimg
     gxdxb23ba1ydlbCpPGmHY/Zmx0YB6SXPjjx/YddOtoiDKYuIlAfP/mW0uNElp1ZIqW
     vWLlTEN3NU5Kq+CpYF0G1FhGz9RGTEQaRMUNjZS8=
Message-ID: <5395C301.9030904@internest.it>
Date: Mon, 09 Jun 2014 16:21:53 +0200
From: Info Internest <info@internest.it>
User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64; rv:24.0) Gecko/20100101 Thunderbird/24.5.0
MIME-Version: 1.0
To: mypersonal@gmail.com
Subject: Invio codice
Content-Type: text/plain; charset=ISO-8859-15; format=flowed
Content-Transfer-Encoding: 7bit

ciao bello ti invio il codice la prossima volta fammi sapere

My answer:


So, Gmail tells you:

Why is this message in Spam? It’s similar to messages that have been detected by our spam filters.

This is generally a problem with spammy looking content.

And indeed, if I received a message containing “ciao bello ti invio il codice la prossima volta fammi sapere” I’d probably mark it as spam too. It’s certainly spammy looking enough.

You can do two things:

  1. Rewrite your content to be more professional in nature.
  2. Click “Not Spam” a lot.

View the full question and answer on Server Fault.

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