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Recently I've been seeing some instances of Your access to this mail system has been rejected due to the sending MTA's poor reputation. in my maillog and have noticed that my emails have been getting sent to the spam inbox in Gmail, Yahoo, and hotmail.

Here's the full source of one of the emails:

Received: by with SMTP id e1csp154999qee;
        Fri, 19 Apr 2013 14:27:55 -0700 (PDT)
X-Received: by with SMTP id gj1mr21470844pbb.13.1366406875534;
        Fri, 19 Apr 2013 14:27:55 -0700 (PDT)
Return-Path: <>
Received: from ([2600:3c00::f03c:91ff:fedf:7f03])
        by with ESMTPS id n6si13604221pan.304.2013.
        (version=TLSv1.2 cipher=RC4-SHA bits=128/128);
        Fri, 19 Apr 2013 14:27:55 -0700 (PDT)
Received-SPF: pass ( domain of designates 2600:3c00::f03c:91ff:fedf:7f03 as permitted sender) client-ip=2600:3c00::f03c:91ff:fedf:7f03;
       spf=pass ( domain of designates 2600:3c00::f03c:91ff:fedf:7f03 as permitted sender);
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed;; s=apollo;
    h=Content-Type:MIME-Version:To:From:Subject:Date:Message-ID; bh=OKfjRX8q8QVR93ic03qpeWwKr9GAGCpoijICdpzHpiM=;
Received: from acadaware (
    by with local-smtp (Exim 4.80)
    (envelope-from <>)
    id 1UTIqY-0007O5-Nu
    for; Fri, 19 Apr 2013 21:27:54 +0000
Message-ID: <>
Date: Fri, 19 Apr 2013 17:27:54 -0400
Subject: Acadaware Account Password Reset
From: Acadaware Accounts <>
MIME-Version: 1.0
Content-Type: multipart/alternative;

Content-Type: text/html; charset=utf-8
Content-Transfer-Encoding: quoted-printable

    You, or someone else, has requested a password reset for your Ac= account.<br />
    If you did not make this request you may=
 ignore this message.

    Visit this link to s=
et your password<br />
    <a href=3D"https://portal.acadaw=">https://portal=</a>

    This password reset link will expire after 5 hou=
    , after you change your password, or after you've sucessfully lo=
gged in.

<p style=3D"font-size:small; color: #666;">=

    &mdash;<br />
    This message was automatically sent by <a hr=


I've never had any problems until recently. Something that may correlate with this is that I had to re-provision the server sending mail and reconfigure EXIM4, however I mostly just copied the old configuration settings, so I don't believe this is the problem. I did change the hostname of the machine, but again, I'm not sure if this is the problem.

I suspected I may be on a blacklist, but have checked all of the lists mentioned in related questions and they've all come back green.

Any ideas?

share|improve this question
It appears your domain is configured to use Google apps and is sending from your server (which is permitted with your SPF as it includes your A record) however, your server isn't listening on port 25, which doesn't seem legitimate. Have you tried restoring exim to listen on port 25? – Andrew Ty. Apr 19 '13 at 22:36
you're sending via IPv6, but your ipv6 address 2600:3c00::f03c:91ff:fedf:7f03 has no reverse DNS (PTR). – Gryphius Apr 20 '13 at 9:16
@Gryphius Good catch. I hadn't realized this. I did have a PTR record for my v4 address. When Gmail switched over to IPv6 back on v6 day I didn't have any problems. Also, it doesn't look like hotmail or yahoo use IPv6 and they're still dropping my mail into spam. – Evan Purkhiser Apr 20 '13 at 21:24
@AndrewTy. I haven't tried opening port 25. I've never had port 25 open, and have never intended to receive mail on the server. It hasn't seemed to be a problem before. – Evan Purkhiser Apr 20 '13 at 21:25

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