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Thunderbird creates wrong digital S/MIME signature for emails with "Content-Transfer-Encoding: quoted-printable"

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  • 0 sa na da wannan matsala
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  • Amsa ta ƙarshe daga tobias.knauss

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Thunderbird 102.5.0, 64 bit, on Win 10 Pro 22H2

I have multiple email accounts in my Thunderbird, and 2 of them have S/MIME certificates. The digital signing of emails by default is enabled in both accounts. The certificates are valid and not expired. Today I had sent a signed email (not encrypted) from one of these two accounts to the other one, and I noticed that the S/MIME icon in the received email has a red exclamation mark. When I click on it, the message box says "Digital Signature Is Not Valid". I did several tests and found, that this only happens when the email contains non-ASCII characters and the encoding changes from "Content-Transfer-Encoding: 7bit" to "Content-Transfer-Encoding: quoted-printable".

The easiest way to reproduce is: Send an digitally signed, but not encrypted email from an email account with S/MIME certificate to any other email account. The subject is empty, the email body contains only one single character: "ä". (German Umlaut, a with 2 dots above it). You may also use other characters like "ö, ü, ß, €".

The wrong signature in the received email is noticed not only by Thunderbird, but also by other email software (e.g. Android FairEmail), which means the failure happens during creation of the email in Thunderbird and it's not a decoding problem of Thunderbird.

I also managed somehow to send emails with text that contains these characters and has "Content-Transfer-Encoding: 8bit"; however, these emails are signed correctly.

Please tell me whether I should open a bug report in bugzilla.mozilla.org; I assume that Product="MailNews Core" and Comp="Security: S/MIME" would be the right parameters.

Here's the source of one of the faulty emails (subject="Test", body="ß"). Since the email contains only the public key, it should be no problem to reveal it.

From - Wed Nov 30 09:25:08 2022 X-Account-Key: account1 X-UIDL: 1N0WD8-1omBrr2Q20-00wR6n X-Mozilla-Status: 0001 X-Mozilla-Status2: 00000000 X-Mozilla-Keys: Return-Path: <tobias.knauss@web.de> Authentication-Results: web.de; dkim=pass header.i=@web.de Received: from mout.web.de ([212.227.17.11]) by mx-ha.web.de (mxweb102

[212.227.17.8]) with ESMTPS (Nemesis) id 1MOzOo-1pNSUp1yMW-00PPjD for
<Tobias.Knauss@web.de>; Wed, 30 Nov 2022 09:25:07 +0100

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=web.de; s=s29768273; t=1669796707; bh=SDq5umjzV3wYXY36JV/aVkzI8u3Hf2Hec8CCGNwtB9w=; h=X-UI-Sender-Class:Date:To:From:Subject; b=FbQ67rifktxP9nM8sz3D36tt/ZsaY2Vi1OmdY9oOBI2WroXYPpeXudVNEhf84siT6 swNCVIXj9UKx/dqzVjOIycuyqJfOODWeLHtIQ1YnYcOAsQeb/0PzS0HH8cWn+ZQCF1 S7IzhcMGq1wI94c7x650tL6Rb046Ec5AH7DGpT11eAXluml5L0WrP06avgaZyfXfbt oY1Ysx01hJAxDtBRiozAO+oXl+olvn8q3PNucZ99C74qO/8diNyeuoNIDoVbcG1VmS AJ6vRcP9qOFcFxASQH9aEyBQFGTMHbkJfvmZ+/uSRX8c6g3c4SJKlj2GtFAVP7aD+W +8x+5P1HSy13A== X-UI-Sender-Class: 814a7b36-bfc1-4dae-8640-3722d8ec6cd6 Received: from [10.1.0.62] ([79.239.239.241]) by smtp.web.de (mrweb106

[213.165.67.124]) with ESMTPSA (Nemesis) id 1MqIB7-1odclE14Vf-00nFub for
<Tobias.Knauss@web.de>; Wed, 30 Nov 2022 09:25:07 +0100

Message-ID: <36ee3171-8269-1aaa-b283-3a8e75490704@web.de> Date: Wed, 30 Nov 2022 09:25:06 +0100 MIME-Version: 1.0 User-Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:102.0) Gecko/20100101

Thunderbird/102.5.0

To: =?UTF-8?Q?Tobias_Knau=c3=9f?= <Tobias.Knauss@web.de> From: =?UTF-8?Q?Tobias_Knau=c3=9f?= <tobias.knauss@web.de> Subject: Test Content-Type: multipart/signed; protocol="application/pkcs7-signature"; micalg=sha-256; boundary="------------ms070608090501000005000908" X-Provags-ID: V03:K1:3fHBG1RsWkNgUbiHxoKZ6EIu4iy/Aw1ojrSACjcJnBJOa5AXJUg

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8Xh464uCkIGtE2ET05Jkw==

X-Spam-Flag: NO UI-OutboundReport: notjunk:1;M01:P0:hLucRX0RZTU=;sZIYbhwfM2hn0+2CD9AF2J9SpIE

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Envelope-To: <Tobias.Knauss@web.de> UI-InboundReport: unknown:5;M01:P0:nHmIiTtIVZM=;mWHVQETSzLIqUj2DPgkPLBuSL3cD

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X-AVK-Virus-Check: AVA 25.34594;8A26DEF X-AVK-Spam-Check: 1;str=0001.0A782F29.63871365.0027,ss=1,re=0.000,recu=0.000,reip=0.000,cl=1,cld=1,fgs=0;F1206

This is a cryptographically signed message in MIME format.


ms070608090501000005000908

Content-Type: text/plain; charset=UTF-8; format=flowed Content-Transfer-Encoding: quoted-printable

=C3=9F


ms070608090501000005000908

Content-Type: application/pkcs7-signature; name="smime.p7s" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="smime.p7s" Content-Description: S/MIME Cryptographic Signature

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ms070608090501000005000908--
Thunderbird 102.5.0, 64 bit, on Win 10 Pro 22H2 I have multiple email accounts in my Thunderbird, and 2 of them have S/MIME certificates. The digital signing of emails by default is enabled in both accounts. The certificates are valid and not expired. Today I had sent a signed email (not encrypted) from one of these two accounts to the other one, and I noticed that the S/MIME icon in the received email has a red exclamation mark. When I click on it, the message box says "Digital Signature Is Not Valid". I did several tests and found, that this only happens when the email contains non-ASCII characters and the encoding changes from "Content-Transfer-Encoding: 7bit" to "Content-Transfer-Encoding: quoted-printable". The easiest way to reproduce is: Send an digitally signed, but not encrypted email from an email account with S/MIME certificate to any other email account. The subject is empty, the email body contains only one single character: "ä". (German Umlaut, a with 2 dots above it). You may also use other characters like "ö, ü, ß, €". The wrong signature in the received email is noticed not only by Thunderbird, but also by other email software (e.g. Android FairEmail), which means the failure happens during creation of the email in Thunderbird and it's not a decoding problem of Thunderbird. I also managed somehow to send emails with text that contains these characters and has "Content-Transfer-Encoding: 8bit"; however, these emails are signed correctly. Please tell me whether I should open a bug report in bugzilla.mozilla.org; I assume that Product="MailNews Core" and Comp="Security: S/MIME" would be the right parameters. Here's the source of one of the faulty emails (subject="Test", body="ß"). Since the email contains only the public key, it should be no problem to reveal it. From - Wed Nov 30 09:25:08 2022 X-Account-Key: account1 X-UIDL: 1N0WD8-1omBrr2Q20-00wR6n X-Mozilla-Status: 0001 X-Mozilla-Status2: 00000000 X-Mozilla-Keys: Return-Path: <tobias.knauss@web.de> Authentication-Results: web.de; dkim=pass header.i=@web.de Received: from mout.web.de ([212.227.17.11]) by mx-ha.web.de (mxweb102 [212.227.17.8]) with ESMTPS (Nemesis) id 1MOzOo-1pNSUp1yMW-00PPjD for <Tobias.Knauss@web.de>; Wed, 30 Nov 2022 09:25:07 +0100 DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=web.de; s=s29768273; t=1669796707; bh=SDq5umjzV3wYXY36JV/aVkzI8u3Hf2Hec8CCGNwtB9w=; h=X-UI-Sender-Class:Date:To:From:Subject; b=FbQ67rifktxP9nM8sz3D36tt/ZsaY2Vi1OmdY9oOBI2WroXYPpeXudVNEhf84siT6 swNCVIXj9UKx/dqzVjOIycuyqJfOODWeLHtIQ1YnYcOAsQeb/0PzS0HH8cWn+ZQCF1 S7IzhcMGq1wI94c7x650tL6Rb046Ec5AH7DGpT11eAXluml5L0WrP06avgaZyfXfbt oY1Ysx01hJAxDtBRiozAO+oXl+olvn8q3PNucZ99C74qO/8diNyeuoNIDoVbcG1VmS AJ6vRcP9qOFcFxASQH9aEyBQFGTMHbkJfvmZ+/uSRX8c6g3c4SJKlj2GtFAVP7aD+W +8x+5P1HSy13A== X-UI-Sender-Class: 814a7b36-bfc1-4dae-8640-3722d8ec6cd6 Received: from [10.1.0.62] ([79.239.239.241]) by smtp.web.de (mrweb106 [213.165.67.124]) with ESMTPSA (Nemesis) id 1MqIB7-1odclE14Vf-00nFub for <Tobias.Knauss@web.de>; Wed, 30 Nov 2022 09:25:07 +0100 Message-ID: <36ee3171-8269-1aaa-b283-3a8e75490704@web.de> Date: Wed, 30 Nov 2022 09:25:06 +0100 MIME-Version: 1.0 User-Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:102.0) Gecko/20100101 Thunderbird/102.5.0 To: =?UTF-8?Q?Tobias_Knau=c3=9f?= <Tobias.Knauss@web.de> From: =?UTF-8?Q?Tobias_Knau=c3=9f?= <tobias.knauss@web.de> Subject: Test Content-Type: multipart/signed; protocol="application/pkcs7-signature"; micalg=sha-256; boundary="------------ms070608090501000005000908" X-Provags-ID: V03:K1:3fHBG1RsWkNgUbiHxoKZ6EIu4iy/Aw1ojrSACjcJnBJOa5AXJUg ufKIPya1i38ZJxXpG4yL1RRB3aYOLCc/haGkmwXwwAfJi/t90zh7gS7kt0uxqTDhdcZX9Sf B6gtnEDF5AlIxJ9w6rKDIOEUgbtVfW8gbVKvDrTH9B6OnKZCSv4U2HZU3LBwQ7pFcdsNYO2 8Xh464uCkIGtE2ET05Jkw== X-Spam-Flag: NO UI-OutboundReport: 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I just checked the sent emails in the "Sent" folder. These emails are fine, and their encoding is "Content-Transfer-Encoding: 8bit". Why is the encoding different from the received email? What goes wrong here?

Here's the source of one of the outgoing emails (should be the one that belongs to the received one above):

From - Wed, 30 Nov 2022 08:31:39 GMT X-Mozilla-Status: 0001 X-Mozilla-Status2: 00800000 Message-ID: <16bc6395-5bf8-04d5-db8a-6e0053055f14@web.de> Date: Wed, 30 Nov 2022 09:31:38 +0100 MIME-Version: 1.0 User-Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:102.0) Gecko/20100101

Thunderbird/102.5.0

To: =?UTF-8?Q?Tobias_Knau=c3=9f?= <Tobias.Knauss@web.de> From: =?UTF-8?Q?Tobias_Knau=c3=9f?= <tobias.knauss@web.de> Subject: Test Content-Type: multipart/signed; protocol="application/pkcs7-signature"; micalg=sha-256; boundary="------------ms060506050804060200010808"

This is a cryptographically signed message in MIME format.


ms060506050804060200010808

Content-Type: text/plain; charset=UTF-8; format=flowed Content-Transfer-Encoding: 8bit

ß


ms060506050804060200010808

Content-Type: application/pkcs7-signature; name="smime.p7s" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="smime.p7s" Content-Description: S/MIME Cryptographic Signature

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ms060506050804060200010808--

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