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:
Delivered-To: firstname.lastname@example.org Received: by 10.49.3.193 with SMTP id e1csp154999qee; Fri, 19 Apr 2013 14:27:55 -0700 (PDT) X-Received: by 10.68.105.33 with SMTP id gj1mr21470844pbb.13.1366406875534; Fri, 19 Apr 2013 14:27:55 -0700 (PDT) Return-Path: <email@example.com> Received: from apollo.acadaware.com ([2600:3c00::f03c:91ff:fedf:7f03]) by mx.google.com with ESMTPS id n6si13604221pan.304.2013.04.19.14.27.55 (version=TLSv1.2 cipher=RC4-SHA bits=128/128); Fri, 19 Apr 2013 14:27:55 -0700 (PDT) Received-SPF: pass (google.com: domain of firstname.lastname@example.org designates 2600:3c00::f03c:91ff:fedf:7f03 as permitted sender) client-ip=2600:3c00::f03c:91ff:fedf:7f03; Authentication-Results: mx.google.com; spf=pass (google.com: domain of email@example.com designates 2600:3c00::f03c:91ff:fedf:7f03 as permitted sender) firstname.lastname@example.org; dkim=pass email@example.com DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed; d=acadaware.com; s=apollo; h=Content-Type:MIME-Version:To:From:Subject:Date:Message-ID; bh=OKfjRX8q8QVR93ic03qpeWwKr9GAGCpoijICdpzHpiM=; b=Vr34X3Nfi/EcF0WUcUgEXhYH7VdBN0wy9sAPGW7JBC+ENxnQLeKjsX17vNt+/lfaIQPKl8M9kx5hXMAHKvy0KOo8+zCMS1Tg+muddtU+QAYlmSmeOngUC6M7neNCr8e+pE1/95B3/TOmV8X+ABILMYVBk17dEDLARcsWtI3cHrU=; Received: from acadaware (helo=portal.acadaware.com) by apollo.acadaware.com with local-smtp (Exim 4.80) (envelope-from <firstname.lastname@example.org>) id 1UTIqY-0007O5-Nu for email@example.com; Fri, 19 Apr 2013 21:27:54 +0000 Message-ID: <firstname.lastname@example.org> Date: Fri, 19 Apr 2013 17:27:54 -0400 Subject: Acadaware Account Password Reset From: Acadaware Accounts <email@example.com> To: firstname.lastname@example.org MIME-Version: 1.0 Content-Type: multipart/alternative; boundary="_=_swift_v4_13664068745171b6daad629_=_" --_=_swift_v4_13664068745171b6daad629_=_ Content-Type: text/html; charset=utf-8 Content-Transfer-Encoding: quoted-printable <p> You, or someone else, has requested a password reset for your Ac= adaware.com account.<br /> If you did not make this request you may= ignore this message. </p> <p> Visit this link to s= et your Acadaware.com password<br /> <a href=3D"https://portal.acadaw= are.com/password/change/">https://portal= .acadaware.com/password/change/</a> <= /p> <p> This password reset link will expire after 5 hou= rs , after you change your password, or after you've sucessfully lo= gged in. </p> <p style=3D"font-size:small; color: #666;">= —<br /> This message was automatically sent by <a hr= ef=3D"https://portal.acadaware.com">acadaware.com</a> </p> --_=_swift_v4_13664068745171b6daad629_=_--
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.