Emails forwarded via postfix get flagged as spam and forged in Gmail

Posted by Kendall Hopkins on Server Fault See other posts from Server Fault or by Kendall Hopkins
Published on 2012-05-09T17:25:49Z Indexed on 2012/09/09 3:39 UTC
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I'm trying to setup a forwarding only email server. I'm running into the problem where all messages forwarded via postfix are getting put into gmail's spam folder and getting flagged as forged. I'm testing a very similar setup on a cpanel box and their forwarded emails make it through without any problem.

Things I've done:

  • Setup reverse dns on forwarding box
  • Setup SPF record for forwarding box domain

CPanel route (not flagged as spam): [email protected]personaldomain.com -> [email protected]domain.com -> personaluser@gmail.com

AWS postfix route (flagged as spam): [email protected]personaldomain.com -> [email protected]personaldomain2.com -> personaluser@gmail.com

Gmail error message:

/etc/postfix/main.cf

myhostname = sputnik.*domain*.com
smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
biff = no
append_dot_mydomain = no
readme_directory = no
myorigin = /etc/mailname
mydestination = sputnik.*domain*.com, localhost.*domain*.com, , localhost
relayhost = 
mynetworks = 127.0.0.0/8 10.0.0.0/24 [::1]/128 [fe80::%eth0]/64
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all
virtual_alias_maps = hash:/etc/postfix/virtual

Email forwarded by CPanel (doesn't get marked as spam):

Delivered-To: *personaluser*@gmail.com
Received: by 10.182.144.98 with SMTP id sl2csp14396obb;
        Wed, 9 May 2012 09:18:36 -0700 (PDT)
Received: by 10.182.52.38 with SMTP id q6mr1137571obo.8.1336580316700;
        Wed, 09 May 2012 09:18:36 -0700 (PDT)
Return-Path: <[email protected]*personaldomain*.com>
Received: from web6.*domain*.com (173.193.55.66-static.reverse.softlayer.com. [173.193.55.66])
        by mx.google.com with ESMTPS id ec7si1845451obc.67.2012.05.09.09.18.36
        (version=TLSv1/SSLv3 cipher=OTHER);
        Wed, 09 May 2012 09:18:36 -0700 (PDT)
Received-SPF: neutral (google.com: 173.193.55.66 is neither permitted nor denied by best guess record for domain of [email protected]*personaldomain*.com) client-ip=173.193.55.66;
Authentication-Results: mx.google.com; spf=neutral (google.com: 173.193.55.66 is neither permitted nor denied by best guess record for domain of [email protected]*personaldomain*.com) [email protected]*personaldomain*.com
Received: from mail-vb0-f43.google.com ([209.85.212.43]:56152)
    by web6.*domain*.com with esmtps (TLSv1:RC4-SHA:128)
    (Exim 4.77)
    (envelope-from <[email protected]*personaldomain*.com>)
    id 1SS9b2-0007J9-LK
    for [email protected]*domain*.com; Wed, 09 May 2012 12:18:36 -0400
Received: by vbbfq11 with SMTP id fq11so599132vbb.2
        for <[email protected]*domain*.com>; Wed, 09 May 2012 09:18:35 -0700 (PDT)
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=google.com; s=20120113;
        h=mime-version:x-originating-ip:date:message-id:subject:from:to
         :content-type:x-gm-message-state;
        bh=Hr0AH40uUtx/w/u9hltbrhHJhRaD5ubKmz2gGg44VLs=;
        b=IBKi6Xalr9XVFYwdkWxn9PLRB69qqJ9AjUPdvGh8VxMNW4S+hF6r4GJcGOvkDn2drO
         kw5r4iOpGuWUQPEMHRPyO4+Ozc9SE9s4Px2oVpadR6v3hO+utvFGoj7UuchsXzHqPVZ8
         A9FS4cKiE0E0zurTjR7pfQtZT64goeEJoI/CtvcoTXj/Mdrj36gZ2FYtO8Qj4dFXpfu9
         uGAKa4jYfx9zwdvhLzQ3mouWwQtzssKUD+IvyuRppLwI2WFb9mWxHg9n8y9u5IaduLn7
         7TvLIyiBtS3DgqSKQy18POVYgnUFilcDorJs30hxFxJhzfTFW1Gdhrwjvz0MTYDSRiGQ
         P4aw==
MIME-Version: 1.0
Received: by 10.52.173.209 with SMTP id bm17mr326586vdc.54.1336580315681; Wed,
 09 May 2012 09:18:35 -0700 (PDT)
Received: by 10.220.191.134 with HTTP; Wed, 9 May 2012 09:18:35 -0700 (PDT)
X-Originating-IP: [99.50.225.7]
Date: Wed, 9 May 2012 12:18:35 -0400
Message-ID: <[email protected]om>
Subject: test5
From: Kendall Hopkins <[email protected]*personaldomain*.com>
To: [email protected]*domain*.com
Content-Type: multipart/alternative; boundary=bcaec51b9bf5ee11c004bf9cda9c
X-Gm-Message-State: ALoCoQm3t1Hohu7fEr5zxQZsC8FQocg662Jv5MXlPXBnPnx2AiQrbLsNQNknLy39Su45xBMCM47K
X-AntiAbuse: This header was added to track abuse, please include it with any abuse report
X-AntiAbuse: Primary Hostname - web6.*domain*.com
X-AntiAbuse: Original Domain - kendall.*domain*.com
X-AntiAbuse: Originator/Caller UID/GID - [47 12] / [47 12]
X-AntiAbuse: Sender Address Domain - *personaldomain*.com
X-Source: 
X-Source-Args: 
X-Source-Dir: 

--bcaec51b9bf5ee11c004bf9cda9c
Content-Type: text/plain; charset=ISO-8859-1

test5

--bcaec51b9bf5ee11c004bf9cda9c
Content-Type: text/html; charset=ISO-8859-1

test5

--bcaec51b9bf5ee11c004bf9cda9c--

Email forwarded via AWS postfix box (marked as spam):

Delivered-To: *personaluser*@gmail.com
Received: by 10.182.144.98 with SMTP id sl2csp14350obb;
        Wed, 9 May 2012 09:17:46 -0700 (PDT)
Received: by 10.229.137.143 with SMTP id w15mr389471qct.37.1336580266237;
        Wed, 09 May 2012 09:17:46 -0700 (PDT)
Return-Path: <[email protected]*personaldomain*.com>
Received: from sputnik.*domain*.com (sputnik.*domain*.com. [107.21.39.201])
        by mx.google.com with ESMTP id o8si1330855qct.115.2012.05.09.09.17.46;
        Wed, 09 May 2012 09:17:46 -0700 (PDT)
Received-SPF: neutral (google.com: 107.21.39.201 is neither permitted nor denied by best guess record for domain of [email protected]*personaldomain*.com) client-ip=107.21.39.201;
Authentication-Results: mx.google.com; spf=neutral (google.com: 107.21.39.201 is neither permitted nor denied by best guess record for domain of [email protected]*personaldomain*.com) [email protected]*personaldomain*.com
Received: from mail-vb0-f52.google.com (mail-vb0-f52.google.com [209.85.212.52])
    by sputnik.*domain*.com (Postfix) with ESMTP id A308122AD6
    for <[email protected]*personaldomain2*.com>; Wed,  9 May 2012 16:17:45 +0000 (UTC)
Received: by vbzb23 with SMTP id b23so448664vbz.25
        for <[email protected]*personaldomain2*.com>; Wed, 09 May 2012 09:17:45 -0700 (PDT)
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=google.com; s=20120113;
        h=mime-version:x-originating-ip:date:message-id:subject:from:to
         :content-type:x-gm-message-state;
        bh=XAzjH9tUXn6SbadVSLwJs2JVbyY4arosdTuV8Nv+ARI=;
        b=U8gIgHd6mhWYqPU4MH/eyvo3kyZsDn/GiYwZj5CLbs6Zz/ZOXQkenRi7zW3ewVFi/9
         uAFylT8SQ+Wjw2l6OgAioCTojfZ58s4H/JW+1bu460KAP9aeOTcZDNSsHlsj0wvH5XRV
         4DQJa11kz+WFVtVVcFuB33WVUPAgJfXzY+pSTe+FWsrZyrrwL7/Vm9TSKI5PBwRN9i4g
         zAZabgkmw1o2THT3kbJi6vAbPzlqK2LVbgt82PP0emHdto7jl4iD5F6lVix4U0dsrtRv
         xuGUE0gDyIwJuR4Q5YTkNubwGH/Y2bFBtpx2q1IORANrolWxIGaZSceUWawABkBGPABX
         1/eg==
MIME-Version: 1.0
Received: by 10.52.96.169 with SMTP id dt9mr282954vdb.107.1336580265812; Wed,
 09 May 2012 09:17:45 -0700 (PDT)
Received: by 10.220.191.134 with HTTP; Wed, 9 May 2012 09:17:45 -0700 (PDT)
X-Originating-IP: [99.50.225.7]
Date: Wed, 9 May 2012 12:17:45 -0400
Message-ID: <[email protected]om>
Subject: test4
From: Kendall Hopkins <[email protected]*personaldomain*.com>
To: [email protected]*personaldomain2*.com
Content-Type: multipart/alternative; boundary=20cf307f37f6f521b304bf9cd79d
X-Gm-Message-State: ALoCoQkrNcfSTWz9t6Ir87KEYyM+zJM4y1AbwP86NMXlk8B3ALhnis+olFCKdgPnwH/sIdzF3+Nh

--20cf307f37f6f521b304bf9cd79d
Content-Type: text/plain; charset=ISO-8859-1

test4

--20cf307f37f6f521b304bf9cd79d
Content-Type: text/html; charset=ISO-8859-1

test4

--20cf307f37f6f521b304bf9cd79d--

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