When sending a reply to a reply to a reply from Hotmail's webmail interface, Hotmail is inserting a X-OriginalArrivalTime header and 2 blank lines in the middle of the multi-line References header is generates.

As a result, the messages headers are broken, and any headers after that are not used. In particular, the MIME-Version header is lost causing rendering problems in email software that is strictly RFC complient.

Here is a small excerpt of an affected message headers. This is taken as a packet sniff between a Hotmail server and a mail server I control so it can be sure that this is the form it is leaving hotmail as, not my mail server adding the header.

In-Reply-To: <{removed email address}>.
References: <{removed email address}>.
 <{removed email address}>.
X-OriginalArrivalTime: 01 Oct 2009 21:47:35.0093 (UTC) FILETIME=[C94E2650:01CA42E0].
.
.
 <{removed email address}>.
MIME-Version: 1.0.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/plain; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.

I will post the full packet sniff in a reply, since I keep getting errors when I post this with the full sniff included.

###
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
......
###
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
EHLO blu0-omc1-s38.blu0.hotmail.com.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250-mx1.ctgameinfo.com.
250-PIPELINING.
250-SIZE 10240000.
250-VRFY.
250-ETRN.
250-AUTH LOGIN PLAIN.
250-AUTH=LOGIN PLAIN.
250-ENHANCEDSTATUSCODES.
250-8BITMIME.
250 DSN.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
MAIL FROM:<{removed email address}> SIZE=3587.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250 2.1.0 Ok.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
RCPT TO:<{removed email address}>.

#
T 83.18.80.98:56248 -> 67.228.21.224:25 [A]
......
#
T 67.228.21.224:25 -> 83.18.80.98:56248 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

####
T 83.18.80.98:56248 -> 67.228.21.224:25 [AP]
EHLO axc98.internetdsl.tpnet.pl.

#
T 67.228.21.224:25 -> 83.18.80.98:56248 [AP]
250-mx1.ctgameinfo.com.
250-PIPELINING.
250-SIZE 10240000.
250-VRFY.
250-ETRN.
250-AUTH LOGIN PLAIN.
250-AUTH=LOGIN PLAIN.
250-ENHANCEDSTATUSCODES.
250-8BITMIME.
250 DSN.

#
T 83.18.80.98:2913 -> 67.228.21.224:25 [A]
......
#
T 67.228.21.224:25 -> 83.18.80.98:2913 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250 2.1.5 Ok.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
DATA.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
354 End data with <CR><LF>.<CR><LF>.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
Received: from BLU149-W41 ([65.55.116.8]) by blu0-omc1-s38.blu0.hotmail.com with Microsoft SMTPSVC(6.0.3790.3959);.
. Thu, 1 Oct 2009 14:47:35 -0700.
Message-ID: <{removed email address}>.
Return-Path: {removed email address}.
Content-Type: multipart/alternative;.
.boundary="_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_".
X-Originating-IP: [69.31.174.220].
From: "cstdenis ." <{removed email address}>.
To: <{removed email address}>.
Subject: RE: test message.
Date: Thu, 1 Oct 2009 21:47:34 +0000.
Importance: Normal.
In-Reply-To: <{removed email address}>.
References: <{removed email address}>.
 <{removed email address}>.
X-OriginalArrivalTime: 01 Oct 2009 21:47:35.0093 (UTC) FILETIME=[C94E2650:01CA42E0].
.
.
 <{removed email address}>.
MIME-Version: 1.0.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/plain; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
.
Test.
.
----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net.
.
.
.
Date: Thu=2C 24 Sep 2009 15:40:09 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: RE: test message.
.
Another reply from Roundcube.
.
=20.
.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." <{removed email address}>=.
 wrote:.
.
 This is a test reply.
.
.
.
.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: test mes
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
sage.
.
test message body.
.
.
--=20.
this si a test sig.
.
.
.
.
Insert movie times and more without leaving Hotmail=AE. See how..
=20.
.
.
--=20.
this si a test sig.
 .. .   ..  =0A=.
_________________________________________________________________=0A=.
Insert movie times and more without leaving Hotmail=AE.=0A=.
http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tut=.
orial_QuickAdd_062009=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/html; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
<html>.
<head>.
<style><!--.
..hmmessage P.
{.
margin:0px=3B.
padding:0px.
}.
body.hmmessage.
{.
font-size: 10pt=3B.
font-family:Verdana.
}.
--></style>.
</head>.
<body class=3D'hmmessage'>.
Test<br><br>----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net<br><br><br><br><hr id=3D"stopSpelling">Date: T=.
hu=2C 24 Sep 2009 15:40:09 -0700<br>From: {removed email address}<br>To: cstdenis@=.
hotmail.com<br>Subject: RE: test message<br><br>Another reply from Roundcub=.
e<BR>.
&nbsp=3B<BR>.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." &lt={removed email address}=.
..com&gt=3B wrote:<BR>.
<blockquote style=3D"border-left: 2px solid rgb(16=2C 16=2C 255)=3B padding=.
-left: 5px=3B margin-left: 5px=3B width: 100%=3B"> This is a test reply<br>=.
<br><br>.
<hr id=3D"ecxstopSpelling">.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700<br>From: {removed email address}<br>To: cs=.
{removed email address}<br>Subj
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
ect: test message<br><br>test message body<br>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div>.
<br>.
<hr>.
Insert movie times and more without leaving Hotmail=AE. <a href=3D"http://w=.
indowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tutorial_Qu=.
ickAdd_062009">See how.</a></blockquote>.
&nbsp=3B<BR>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div> .. .   ..  <br /><hr />Insert movie times and more without leaving H=.
otmail=AE. <a href=3D'http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=.
=3DTXT_TAGLM_WL_HM_Tutorial_QuickAdd_062009' target=3D'_new'>See how.</a></=.
body>.
</html>=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_--.
..

###
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
......
###
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
EHLO blu0-omc1-s38.blu0.hotmail.com.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250-mx1.ctgameinfo.com.
250-PIPELINING.
250-SIZE 10240000.
250-VRFY.
250-ETRN.
250-AUTH LOGIN PLAIN.
250-AUTH=LOGIN PLAIN.
250-ENHANCEDSTATUSCODES.
250-8BITMIME.
250 DSN.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
MAIL FROM:<{removed email address}> SIZE=3587.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250 2.1.0 Ok.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
RCPT TO:<{removed email address}>.

#
T 83.18.80.98:56248 -> 67.228.21.224:25 [A]
......
#
T 67.228.21.224:25 -> 83.18.80.98:56248 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

####
T 83.18.80.98:56248 -> 67.228.21.224:25 [AP]
EHLO axc98.internetdsl.tpnet.pl.

#
T 67.228.21.224:25 -> 83.18.80.98:56248 [AP]
250-mx1.ctgameinfo.com.
250-PIPELINING.
250-SIZE 10240000.
250-VRFY.
250-ETRN.
250-AUTH LOGIN PLAIN.
250-AUTH=LOGIN PLAIN.
250-ENHANCEDSTATUSCODES.
250-8BITMIME.
250 DSN.

#
T 83.18.80.98:2913 -> 67.228.21.224:25 [A]
......
#
T 67.228.21.224:25 -> 83.18.80.98:2913 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250 2.1.5 Ok.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
DATA.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
354 End data with <CR><LF>.<CR><LF>.

###
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
......
###
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
EHLO blu0-omc1-s38.blu0.hotmail.com.

#
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
250-mx1.ctgameinfo.com.
250-PIPELINING.
250-SIZE 10240000.
250-VRFY.
250-ETRN.
250-AUTH LOGIN PLAIN.
250-AUTH=LOGIN PLAIN.
250-ENHANCEDSTATUSCODES.
250-8BITMIME.
250 DSN.

###
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
......
###
T 67.228.21.224:25 -> 65.55.116.49:23588 [AP]
220 mx1.ctgameinfo.com ESMTP Postfix.

T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
Received: from BLU149-W41 ([65.55.116.8]) by blu0-omc1-s38.blu0.hotmail.com with Microsoft SMTPSVC(6.0.3790.3959);.
. Thu, 1 Oct 2009 14:47:35 -0700.
Message-ID: <{removed email address}>.
Return-Path: {removed email address}.
Content-Type: multipart/alternative;.
.boundary="_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_".
X-Originating-IP: [69.31.174.220].
From: "cstdenis ." <{removed email address}>.
To: <{removed email address}>.
Subject: RE: test message.
Date: Thu, 1 Oct 2009 21:47:34 +0000.
Importance: Normal.
In-Reply-To: <{removed email address}>.
References: <{removed email address}>.
 <{removed email address}>.
X-OriginalArrivalTime: 01 Oct 2009 21:47:35.0093 (UTC) FILETIME=[C94E2650:01CA42E0].
.
.
 <{removed email address}>.
MIME-Version: 1.0.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/plain; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
.
Test.
.
----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net.
.
.
.
Date: Thu=2C 24 Sep 2009 15:40:09 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: RE: test message.
.
Another reply from Roundcube.
.
=20.
.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." <{removed email address}>=.
 wrote:.
.
 This is a test reply.
.
.
.
.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: test mes
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
sage.
.
test message body.
.
.
--=20.
this si a test sig.
.
.
.
.
Insert movie times and more without leaving Hotmail=AE. See how..
=20.
.
.
--=20.
this si a test sig.
 .. .   ..  =0A=.
_________________________________________________________________=0A=.
Insert movie times and more without leaving Hotmail=AE.=0A=.
http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tut=.
orial_QuickAdd_062009=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/html; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
<html>.
<head>.
<style><!--.
..hmmessage P.
{.
margin:0px=3B.
padding:0px.
}.
body.hmmessage.
{.
font-size: 10pt=3B.
font-family:Verdana.
}.
--></style>.
</head>.
<body class=3D'hmmessage'>.
Test<br><br>----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net<br><br><br><br><hr id=3D"stopSpelling">Date: T=.
hu=2C 24 Sep 2009 15:40:09 -0700<br>From: {removed email address}<br>To: cstdenis@=.
hotmail.com<br>Subject: RE: test message<br><br>Another reply from Roundcub=.
e<BR>.
&nbsp=3B<BR>.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." &lt={removed email address}=.
..com&gt=3B wrote:<BR>.
<blockquote style=3D"border-left: 2px solid rgb(16=2C 16=2C 255)=3B padding=.
-left: 5px=3B margin-left: 5px=3B width: 100%=3B"> This is a test reply<br>=.
<br><br>.
<hr id=3D"ecxstopSpelling">.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700<br>From: {removed email address}<br>To: cs=.
{removed email address}<br>Subj
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
ect: test message<br><br>test message body<br>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div>.
<br>.
<hr>.
Insert movie times and more without leaving Hotmail=AE. <a href=3D"http://w=.
indowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tutorial_Qu=.
ickAdd_062009">See how.</a></blockquote>.
&nbsp=3B<BR>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div> .. .   ..  <br /><hr />Insert movie times and more without leaving H=.
otmail=AE. <a href=3D'http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=.
=3DTXT_TAGLM_WL_HM_Tutorial_QuickAdd_062009' target=3D'_new'>See how.</a></=.
body>.
</html>=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_--.
..

Received: from BLU149-W41 ([65.55.116.8]) by blu0-omc1-s38.blu0.hotmail.com with Microsoft SMTPSVC(6.0.3790.3959);.
. Thu, 1 Oct 2009 14:47:35 -0700.
Message-ID: <{removed email address}>.
Return-Path: {removed email address}.
Content-Type: multipart/alternative;.
.boundary="_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_".
X-Originating-IP: [69.31.174.220].
From: "cstdenis ." <{removed email address}>.
To: <{removed email address}>.
Subject: RE: test message.
Date: Thu, 1 Oct 2009 21:47:34 +0000.
Importance: Normal.
In-Reply-To: <{removed email address}>.
References: <{removed email address}>.
 <{removed email address}>.
X-OriginalArrivalTime: 01 Oct 2009 21:47:35.0093 (UTC) FILETIME=[C94E2650:01CA42E0].
.
.
 <{removed email address}>.
MIME-Version: 1.0.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/plain; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
.
Test.
.
----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net.
.
.
.
Date: Thu=2C 24 Sep 2009 15:40:09 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: RE: test message.
.
Another reply from Roundcube.
.
=20.
.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." <{removed email address}>=.
 wrote:.
.
 This is a test reply.
.
.
.
.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700.
From: {removed email address}.
To: {removed email address}.
Subject: test mes
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [A]
sage.
.
test message body.
.
.
--=20.
this si a test sig.
.
.
.
.
Insert movie times and more without leaving Hotmail=AE. See how..
=20.
.
.
--=20.
this si a test sig.
 .. .   ..  =0A=.
_________________________________________________________________=0A=.
Insert movie times and more without leaving Hotmail=AE.=0A=.
http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tut=.
orial_QuickAdd_062009=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_.
Content-Type: text/html; charset="iso-8859-1".
Content-Transfer-Encoding: quoted-printable.
.
<html>.
<head>.
<style><!--.
..hmmessage P.
{.
margin:0px=3B.
padding:0px.
}.
body.hmmessage.
{.
font-size: 10pt=3B.
font-family:Verdana.
}.
--></style>.
</head>.
<body class=3D'hmmessage'>.
Test<br><br>----.
Cstdenis.
http://www.CTgameinfo.com.
http://FanartCentral.cjb.net<br><br><br><br><hr id=3D"stopSpelling">Date: T=.
hu=2C 24 Sep 2009 15:40:09 -0700<br>From: {removed email address}<br>To: cstdenis@=.
hotmail.com<br>Subject: RE: test message<br><br>Another reply from Roundcub=.
e<BR>.
&nbsp=3B<BR>.
On Thu=2C 24 Sep 2009 22:39:16 +0000=2C "cstdenis ." &lt={removed email address}=.
..com&gt=3B wrote:<BR>.
<blockquote style=3D"border-left: 2px solid rgb(16=2C 16=2C 255)=3B padding=.
-left: 5px=3B margin-left: 5px=3B width: 100%=3B"> This is a test reply<br>=.
<br><br>.
<hr id=3D"ecxstopSpelling">.
Date: Thu=2C 24 Sep 2009 15:38:38 -0700<br>From: {removed email address}<br>To: cs=.
{removed email address}<br>Subj
#
T 65.55.116.49:23588 -> 67.228.21.224:25 [AP]
ect: test message<br><br>test message body<br>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div>.
<br>.
<hr>.
Insert movie times and more without leaving Hotmail=AE. <a href=3D"http://w=.
indowslive.com/Tutorial/Hotmail/QuickAdd?ocid=3DTXT_TAGLM_WL_HM_Tutorial_Qu=.
ickAdd_062009">See how.</a></blockquote>.
&nbsp=3B<BR>.
<div>.
<pre>-- <br>this si a test sig</pre>.
</div> .. .   ..  <br /><hr />Insert movie times and more without leaving H=.
otmail=AE. <a href=3D'http://windowslive.com/Tutorial/Hotmail/QuickAdd?ocid=.
=3DTXT_TAGLM_WL_HM_Tutorial_QuickAdd_062009' target=3D'_new'>See how.</a></=.
body>.
</html>=.
.
--_1adbe0ca-ce21-4c29-a6e0-ea642d006ed0_--.
..

I can't post the full packet sniff or even full message headers because every time I try I get the error from this support system.

Sorry, there was a problem with your last request!

Either the site is offline or an unhandled error occurred. We apologize and have logged the error. Please try your request again or if you know who your site administrator is let them know too.

If you need them, please contact me outside this system at chris [at] smartt.com

Looks like one of my attempts worked regardless of the error message I got. Here is the link

http://windowslivehelp.com/community/t/131755.aspx

I have found exactly the same problem as well. It started happening about 3 weeks? back.... my customers are starting to blame me for the problems, and I really don't have time to explain it's not me... so.... yes... can you people please fix this? ta.