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Will Mayall

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Karma: 10
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As part of testing hosted Exchange servers, I noticed that (ironically) the backup confirmation messages sent by the Kerio server look different when received by an Exchange server. Since the messages from the Kerio server are about as simple as can be, they should look the same.

The Exchange server makes major modifications to messages. It breaks many of the basic rules for an MTA/MDA including:

- Modifying the message body
- Converting the message body to a different content type
- Modifying existing message headers
- Not wrapping long message headers
- Rearranging message headers
- Inserting message headers instead of appending at the top
- Useless Microsoft headers added

The backup message sent by the Kerio server becomes a worst case scenario because, as an 8bit encoded message, Exchange encodes it to base64 which is completely unreadable.

If there is a rule that an MTA/MDA should follow when managing a message, Exchange seems to break it. I should point out that the Kerio server follows the rules very well.

The more I dig, the better the Kerio server looks and the worse the Exchange server looks.

Is what I am seeing partially a result of the way the Exchange hosting company has configured Exchange?

Does Kerio have a doc (white paper) that compares in gory detail the differences between the Exchange and Kerio servers?

At the end of this message is a test of how the two servers managed a plain text test message.

Will Mayall

____________________________________________

Original message source as sent to the sending Kerio server:
Return-Path: <mayall<_a.t_>sender.com>
X-Spam-Status: No, hits=0.0 required=3.0
	tests=AWL: 0.979,BAYES_00: -1.665,TOTAL_SCORE: -0.686
X-Spam-Level: 
User-Agent: Microsoft-Entourage/12.15.0.081119
Date: Mon, 05 Jan 2009 08:49:25 -0800
Subject: Plain Text Test Message
From: Will Mayall <mayall<_a.t_>sender.com>
To: Will Mayall <mayall<_a.t_>recipient1.com>,
	<mayall<_a.t_>recipient2.com>
Message-ID: <C5877A15.185AD9%mayall<_a.t_>sender.com>
Thread-Topic: Plain Text Test Message
Thread-Index: AclvVZDbh57uUHS/x0uoRqZ6S58HHA==
Mime-version: 1.0
Content-type: text/plain;
	charset="US-ASCII"
Content-transfer-encoding: 7bit

This is a plain text message sent as a test.

Will

Message as received from a second Kerio server -- simple and clean:
Received: from mail.kerio-sending.com ([207.111.201.59])
	by mail.kerio-receiving.com (Kerio MailServer 6.6.2)
	(using TLSv1/SSLv3 with cipher AES256-SHA (256 bits))
	for mayall<_a.t_>recipient1.com;
	Mon, 5 Jan 2009 08:49:50 -0800
Received: from [76.103.43.250] ([76.103.43.250])
	by mail.kerio-sending.com (Kerio MailServer 6.6.2);
	Mon, 5 Jan 2009 08:49:25 -0800
User-Agent: Microsoft-Entourage/12.15.0.081119
Date: Mon, 05 Jan 2009 08:49:25 -0800
Subject: Plain Text Test Message
From: Will Mayall <mayall<_a.t_>sender.com>
To: Will Mayall <mayall<_a.t_>recipient1.com>,
	<mayall<_a.t_>recipient2.com>
Message-ID: <C5877A15.185AD9%mayall<_a.t_>sender.com>
Thread-Topic: Plain Text Test Message
Thread-Index: AclvVZDbh57uUHS/x0uoRqZ6S58HHA==
Mime-version: 1.0
Content-type: text/plain;
	charset="US-ASCII"
Content-transfer-encoding: 7bit

This is a plain text message sent as a test.

Will


Message as received from the Exchange server -- mangled. (Note that I have hard wrapped the long message headers that Exchange both inserted and modified.):
Received:  from exmf018-1.msoutlookonline.net (10.254.253.34)
 by EXHUB018-3.exch018.msoutlookonline.net (64.78.17.43)
 with Microsoft SMTP Server (TLS) id 8.1.240.5;
 Mon, 5 Jan 2009 08:49:56 -0800
MIME-Version: 1.0
Content-Type: text/html;
	charset="US-ASCII"
Content-Transfer-Encoding: quoted-printable
Received:  from localhost (localhost.localdomain [127.0.0.1])
    by exmf018-1.msoutlookonline.net (Postfix) with ESMTP id CF59B12857
    for <mayall<_a.t_>recipient2.com>; Mon,  5 Jan 2009 08:49:56 -0800 (PST)
X-MimeOLE: Produced By Microsoft Exchange V8.1
Received:  from exmf018-1.msoutlookonline.net ([127.0.0.1])
 by localhost (exmf018-1.msoutlookonline.net [127.0.0.1])
 (amavisd-new, port 10024)	with ESMTP id QQuUeLehXeHD for
 <mayall<_a.t_>recipient2.com>;	Mon,  5 Jan 2009 08:49:51 -0800 (PST)
Received:  from mail.kerio-sending.com
 (mail.kerio-sending.com [207.111.201.59])
 (using TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits))
 (No client certificate requested)
 by exmf018-1.msoutlookonline.net (Postfix) with ESMTP id 0E35612901
 for <mayall<_a.t_>recipient2.com>; Mon,  5 Jan 2009 08:49:50 -0800 (PST)
Received:  from [76.103.43.250] ([76.103.43.250])
 by mail.kerio-sending.com (Kerio MailServer 6.6.2);
 Mon, 5 Jan 2009 08:49:25 -0800
x-ms-exchange-organization-authas: Anonymous
x-ms-exchange-organization-authsource: EXHUB018-3.exch018.msoutlookonline.net
X-Virus-Scanned: by amavisd-new at exmf018-1.msoutlookonline.net
user-agent: Microsoft-Entourage/12.15.0.081119
Content-class: urn:content-classes:message
Subject: Plain Text Test Message
Date: Mon, 5 Jan 2009 08:49:25 -0800
Message-ID: <C5877A15.185AD9%mayall<_a.t_>sender.com>
X-MS-Has-Attach: 
X-MS-TNEF-Correlator: 
Thread-Topic: Plain Text Test Message
thread-index: AclvVZDbh57uUHS/x0uoRqZ6S58HHA==
From: "Will Mayall" <mayall<_a.t_>sender.com>
To: "Will Mayall" <mayall<_a.t_>recipient1.com>,
	"Will Mayall" <mayall<_a.t_>recipient2.com>

<!DOCTYPE HTML PUBLIC "-//W3C//DTD HTML 3.2//EN">
<HTML>
<HEAD>
<META HTTP-EQUIV=3D"Content-Type" CONTENT=3D"text/html; =
charset=3Dus-ascii">
<META NAME=3D"Generator" CONTENT=3D"MS Exchange Server version =
08.01.0329.000">
<TITLE>Plain Text Test Message</TITLE>
</HEAD>
<BODY>
<!-- Converted from text/plain format -->

<P><FONT SIZE=3D2>This is a plain text message sent as a test.<BR>
<BR>
Will<BR>
<BR>
<BR>
</FONT>
</P>

</BODY>
</HTML>

[Updated on: Mon, 05 January 2009 22:38]

  •  
TorW

Messages: 769
Karma: 9
Send a private message to this user
Welcome to the wonderful world of Microsoft. How do you think Kerio's business idea came about?

MS have seldom followed the rules everybody else abides by, and now you too have seen it happening right before your eyes. In all fairness, some of the stuff you see happening is because the hosting company configured it like that, but most everything Microsoft does with regard to SMTP and internet mail is broken by design.

Just for laughs, I saved the Exchange mail to a text file and ran it through spamassassin on a FreeBSD mail server:

%spamc -R < keriotmp.txt
Content analysis details:   (0.9 points, 4.5 required)

 pts rule name              description
---- ---------------------- --------------------------------------------------
-2.6 BAYES_00               BODY: Bayesian spam probability is 0 to 1%
                            [score: 0.0000]
 1.5 MIME_HTML_ONLY         BODY: Message only has text/html MIME parts
 1.9 INVALID_MSGID          Message-Id is not valid, according to RFC 2822


So you can at least expect SpamAssassin on other systems to add 3.4 points to the score simply because MS doesn't know how to construct a technically correct email according to standards that have been well documented for the last 20 years. For more Microsoft e-mail goodness: check this: http://www.slipstick.com/emo/2003/up031211.htm#ol2003message -id

Kerio Mail Server isn't perfect, and the Outlook Connectors are still in beta in my opinion, but Kerio's focus is fortunately not on selling lots of licenses, but making useful software. Plus, the way KMS is put together means future sysadmins again must know how to build a system and not just install software. Microsoft have ruined a whole generation of techies with their broken, "idiot-proof", mouse-click-fest products.

Exchange is bad for your career.
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