2

I have a problem with signing-milter (http://www.signing-milter.org). The problem is that the -b flag is required, and the -b flag is not recommended because it outputs non-RFC compliant email. However, removing the -b flag result in mails that do not validate S/MIME with the error message "Tampered content". The description of the -b flag is the following:

Causes signing-milter to not break headerlines after a ; Header
              lines  moved  inside  a mime-container while signing must not be
              longer then 76 characters. This switch  disables  the  autobreak
              before signing.

I have tried with running ONLY the signing-milter in-between, and I have also tried with "washing" any RFC-errors off the mail by parsing it with MIME::Parser and then rebuilding the email from the ground up. But something is still wrong. The following mails is without the "washing" filter.


The following mail, is signed correctly with the command:

signing-milter -g postfix -m /var/secure_files/cert/signers.cdb -s inet:9991 -t 60 -u postfix –b &>/dev/null </dev/null &

it will result in the following mail, that validates correctly:

Return-Path: <sebastian@sebbe.eu>
X-Original-To: postmaster@sebbe.eu
Delivered-To: postmaster@sebbe.eu
Received: from Bangatan601 (unknown [192.168.2.3])
    by dns1.sebbe.eu (Postfix) with SMTP id E61E74C01D1
    for <postmaster@sebbe.eu>; Wed, 25 Feb 2015 11:12:41 +0100 (CET)
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=sebbe.eu; s=root;
    t=1424859168; bh=0JJ2CUrz7gs1slXbxbBt0gped0s3PEJ2R6vh4blyqTQ=;
    h=From:To:Subject:Date:From;
    b=bxDrSPc8mTl7jSpHYlc3lDgPywm71Y8nnHFccVllB8yd8tYGh3lkPEQZhGxTTz+sn
     iR8cto0qyBEZM8qNfgQSVD0a2jXdM38/VNB6G49Au252CZ6IsjfQdY9LFkdl7WudXt
     YgYQ5Pnj59kCp4GSacRPHlwxQwZCT3hxwF5VcoPc=
Message-ID: <B385DB0CB2F144BFA9FE47A007A6B077@Bangatan601>
From: "Sebastian Nielsen" <sebastian@sebbe.eu>
To: <postmaster@sebbe.eu>
Subject: test
Date: Wed, 25 Feb 2015 11:12:39 +0100
MIME-Version: 1.0
X-Priority: 3
X-MSMail-Priority: Normal
Importance: Normal
X-Mailer: Microsoft Windows Live Mail 16.4.3528.331
X-MimeOLE: Produced By Microsoft MimeOLE V16.4.3528.331
X-Hashcash: 1:26:150225:postmaster@sebbe.eu::NrJAmsa7evEzktIr:000000000000000000000000000000000000000001h79K
Content-Type: multipart/signed; protocol="application/pkcs7-signature"; micalg="sha-256"; boundary="----162A57F1542DDFAD76008518F14459BD"

This is an S/MIME signed message

------162A57F1542DDFAD76008518F14459BD
Content-Type: multipart/alternative; boundary="----=_NextPart_000_0019_01D050EB.F7C76180"

------=_NextPart_000_0019_01D050EB.F7C76180
Content-Type: text/plain;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

test
------=_NextPart_000_0019_01D050EB.F7C76180
Content-Type: text/html;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

<HTML><HEAD></HEAD>
<BODY dir=3Dltr>
<DIV dir=3Dltr>
<DIV style=3D"FONT-SIZE: 12pt; FONT-FAMILY: 'Calibri'; COLOR: #000000">
<DIV>test</DIV></DIV></DIV></BODY></HTML>

------=_NextPart_000_0019_01D050EB.F7C76180--

------162A57F1542DDFAD76008518F14459BD
Content-Type: application/pkcs7-signature; name="smime.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime.p7s"
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------162A57F1542DDFAD76008518F14459BD--

However, if I remove the -b flag from signing-milter, it gets signed as following:

signing-milter -g postfix -m /var/secure_files/cert/signers.cdb -s inet:9991 -t 60 -u postfix &>/dev/null </dev/null &

It result in this:

Return-Path: <sebastian@sebbe.eu>
X-Original-To: postmaster@sebbe.eu
Delivered-To: postmaster@sebbe.eu
Received: from Bangatan601 (unknown [192.168.2.3])
    by dns1.sebbe.eu (Postfix) with SMTP id 6CDFD4C0969
    for <postmaster@sebbe.eu>; Wed, 25 Feb 2015 10:58:00 +0100 (CET)
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=sebbe.eu; s=root;
    t=1424858297; bh=g681Ani3vbnBMVPvXfhl81tk5PAU2QiaQD7wU8Opt0s=;
    h=From:To:Subject:Date:From;
    b=X4bAU3CenDkFk45IUztPl3sYkEWvOGphwAPBtGbdmtlUQ5Z5Faf1l/7B7Uz+J2lOu
     tdyWgsJ4rHJk0+ZC+R/GxShyc8H9tPyUpinR9psIJJG4bHFmbkcoeykTMCzootnOxO
     +GpHHPUHCwxaqBMDMfOKXgos691KZi++1LRsYThI=
Message-ID: <AA66989B33FB47379BEAE4365DE5394E@Bangatan601>
From: "Sebastian Nielsen" <sebastian@sebbe.eu>
To: <postmaster@sebbe.eu>
Subject: test
Date: Wed, 25 Feb 2015 10:57:53 +0100
MIME-Version: 1.0
X-Priority: 3
X-MSMail-Priority: Normal
Importance: Normal
X-Mailer: Microsoft Windows Live Mail 16.4.3528.331
X-MimeOLE: Produced By Microsoft MimeOLE V16.4.3528.331
X-Hashcash: 1:26:150225:postmaster@sebbe.eu::DwuKWYWY2MN+ZUXB:000000000000000000000000000000000000000003yEF8
Content-Type: multipart/signed;
    protocol="application/pkcs7-signature";
    micalg="sha-256";
    boundary="----FD52A1653AA3980B5C0A3BE3D9993FAB"

This is an S/MIME signed message

------FD52A1653AA3980B5C0A3BE3D9993FAB
Content-Type: multipart/alternative;
    boundary="----=_NextPart_000_0007_01D050E9.E7B05740"

------=_NextPart_000_0007_01D050E9.E7B05740
Content-Type: text/plain;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

test
------=_NextPart_000_0007_01D050E9.E7B05740
Content-Type: text/html;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

<HTML><HEAD></HEAD>
<BODY dir=3Dltr>
<DIV dir=3Dltr>
<DIV style=3D"FONT-SIZE: 12pt; FONT-FAMILY: 'Calibri'; COLOR: #000000">
<DIV>test</DIV></DIV></DIV></BODY></HTML>

------=_NextPart_000_0007_01D050E9.E7B05740--

------FD52A1653AA3980B5C0A3BE3D9993FAB
Content-Type: application/pkcs7-signature; name="smime.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime.p7s"
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NwECAzCCASowLgYIKwYBBQUHAgEWImh0dHA6Ly93d3cuc3RhcnRzc2wuY29tL3Bv
bGljeS5wZGYwgfcGCCsGAQUFBwICMIHqMCcWIFN0YXJ0Q29tIENlcnRpZmljYXRp
b24gQXV0aG9yaXR5MAMCAQEagb5UaGlzIGNlcnRpZmljYXRlIHdhcyBpc3N1ZWQg
YWNjb3JkaW5nIHRvIHRoZSBDbGFzcyAxIFZhbGlkYXRpb24gcmVxdWlyZW1lbnRz
IG9mIHRoZSBTdGFydENvbSBDQSBwb2xpY3ksIHJlbGlhbmNlIG9ubHkgZm9yIHRo
ZSBpbnRlbmRlZCBwdXJwb3NlIGluIGNvbXBsaWFuY2Ugb2YgdGhlIHJlbHlpbmcg
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O1i4rNLtRIfJlP9lVlqJGjp6x5tILb2y57b75xP95yCZeQZXUQ0315hK7lx58MLh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------FD52A1653AA3980B5C0A3BE3D9993FAB--

Which does not validate. (Error message: Tampered content).

Here is an UNSIGNED mail from the same client (Windows Live Mail) that could be used to trace any RFC errors:

From: "Sebastian Nielsen" <sebastian@sebbe.eu>
To: <postmaster@sebbe.eu>
Subject: test
Date: Mon, 2 Mar 2015 23:17:33 +0100
MIME-Version: 1.0
Content-Type: multipart/alternative;
    boundary="----=_NextPart_000_0005_01D0553F.10373AE0"
X-Priority: 3
X-MSMail-Priority: Normal
Importance: Normal
X-Mailer: Microsoft Windows Live Mail 16.4.3528.331
X-MimeOLE: Produced By Microsoft MimeOLE V16.4.3528.331

Det här är ett flerdelat meddelande i MIME-format.

------=_NextPart_000_0005_01D0553F.10373AE0
Content-Type: text/plain;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

test
------=_NextPart_000_0005_01D0553F.10373AE0
Content-Type: text/html;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

<HTML><HEAD></HEAD>
<BODY dir=3Dltr>
<DIV dir=3Dltr>
<DIV style=3D"FONT-SIZE: 12pt; FONT-FAMILY: 'Calibri'; COLOR: #000000">
<DIV>test</DIV></DIV></DIV></BODY></HTML>

------=_NextPart_000_0005_01D0553F.10373AE0--

What is the problem? I asked on the postfix user list and I got the answer that the input is not RFC compliant, but in which way? (So I can add a content filter Before that fixes this problem). The mail is created by Windows Live Mail.

0

I have seen the exact same behavior in Outlook 2013 and Outlook 2016 both falsely reporting signing-milter signed multi-part messages as tampered, will The Bat! v7 Professional (Windows) and Mac Mail (El Capitan) report the same messages as valid.

The problem is caused by either to many carriage return (CR) or line feed (LF) or a combination of both (CRLF) at the end of your message payload.

End of your message payload means the final:

------=_NextPart_000_0005_01D0553F.10373AE0--

in the unsigned/raw message you posted.

It doesn't even matter what client send the message, Outlook to Outlook will fail just like Mac Mail to Outlook.

Seeing you using Windows Live Mail brings me to the assumption that this impacts all mail clients using the Windows mail- and/or crypto-backend.

You can even reliable reproduce this by sending a multi-part message using nothing but telnet/ncat...

So just to be clear here, i am almost 99% sure your mails are properly signed with a valid certificate. It's just Microsoft doing things - again - differently.

Now will i have no idea what the -b switch internally did in signing-milter i am certain it took care of making sure your payload is properly escaped prior to signing it.

"Did" simply because this option seems to have been dropped in the current release (running signing-milter Version 20150308 here) which just outputs

option -b is ignored for compatibily reasons, you may remove it safely

when executed with this argument, and mails of course still failing to validate in Outlook.

So the most obvious workaround really seems be to bump the mails through a additional milter before sending them of to signing-milter.

Since i already have such a custom milter in-place (written in python using libmilter) i could simply adopt my code to take care of this:

...
if mail.is_multipart():
    logging.debug("Stripping tailing line feeds (if any) from multi-part payload")
    new_body = new_body.rstrip()

workflow["repl_body"] = new_body
return workflow

So Outlook finally stops complaining about nothing.

Cheers

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