296587 - MS Outlook S/MIME Encrypted Messages cannot be viewed in Thunderbird

Status: RESOLVED INVALID

(Thunderbird :: Security, defect)

Description

[SS]

User-Agent:       Mozilla/4.0 (compatible; MSIE 6.0; Windows NT 5.1; SV1; .NET CLR 1.1.4322)
Build Identifier: "Thunderbird/1.0.2"

After a lot of reluctance I have just downloaded "Thunderbird 1.0.2".  In 
addition I also have "Enigmail" so I can use my OpenPGP encryption.  I have 
recently imported all my messages from "Outlook 2003".  Some of the message 
have been signed using my X.509 certificates and a lot of these have been 
encrypted by the default MS enhanced cryptographic provider.  These messages I 
have not been able to open, period.  In order to test the integrity I have 
also sent new email messages with my certificates and my OpenPGP public key to 
receipient that I regularly communicate with and the new ones are just fine.  
It is just the ones that I imported from Outlook that has a problem.  I'm 
looking for a solution to recover from this!  I looked thro' the bugzilla for 
about an hour or so but could not find any bug reports of this nature.

This is very reproducible, except that you need to have encrypted emails using 
SMIME imported from Outlook to Thunderbird.

Reproducible: Always

Steps to Reproduce:
1. Use "Outlook 2003" and digitally sign and encrypt messages between a couple 
of individuals.  I use "Thawte Personal Freemail X.509" and "CAcert X.509" 
certificates.  For encryption I used the default "Enhanced MS Cryptographic 
Provider" choice suggested by Outlook, using the same X.509 certificates.

2.  After you have verified that you can open the messages in Outlook without 
any problems. Import the same to Thunderbird/Enigmail.

3.  Insure all the certificate are imported and installed in Thunderbird.
Actual Results:  
Thunderbird will show all the headers, but since the message is digitally 
signed & encrypted the body of the messages will be blank (this has been my 
experience).


Expected Results:  
I was expecting the import to be seamless.  I expected that after importing 
the messages and the X.509 certificates I would be able to read the messages.  
Alas that was not the case.  I was intending to get rid of Outlook.  Maybe not 
yet or is it never???

Comment 1

[Frank Wein [:mcsmurf]]

Could you post/attach one such example of a mail here (iirc your have to press
Ctrl+U to get the source, if you want you can skip the mail body, the important
thing is the formatting of the mail)? So you also selected the certificate for
that account you imported the mails into under Security (in the Account Settings)?

Comment 2

[SS]

(In reply to comment #1)
> Could you post/attach one such example of a mail here (iirc your have to press
> Ctrl+U to get the source, if you want you can skip the mail body, the important
> thing is the formatting of the mail)? So you also selected the certificate for
> that account you imported the mails into under Security (in the Account Settings)?

Dear Frank:

Sorry this is the earliest I could get back in to check the status.  At any rate
the following is the encrypted email of-course.  I've masked many fields in the
transcript below for security and privacy reasons.  I'm really hoping this can
make the difference.

Please understand that the original message in Outlook can still be unencrypted
and read there.  However, when I open the message after importing it to "Tbird"
has no X.509 certificates and shows up as a blank email.  I have about 15 to 20
message like this that were encrypted.  There are a couple of initial emails
with X.509 signatures only that open just fine.  I have essentially lost all the
encrypted ones.

From - Sun, 22 May 2005 00:16:21
X-Mozilla-Status: 0001
X-Mozilla-Status2: 10000000
X-Mail-Domail-Received: 6ccd79405fd25b062af9c9d9e10786249ee66b59
Delivered-To: [e-mail]
Received: by XX.XX.XX.XX with SMTP id 00c00000wrr;
        Sat, 21 May 2005 09:12:12 -0700 (PDT)
Received: by 00.00.00.00 with SMTP id 00mr0000000rnx;
        Sat, 21 May 2005 09:12:12 -0700 (PDT)
Return-Path: <[e-mail]>
Received: from pop-a000c00.aaa.bb.mmmmmmmmm.net
(pop-a000c00.aaa.bb.mmmmmmmmm.net [000.000.000.000])
        by mx.some-domain.com with ESMTP id b00si000000rne.2005.05.21.09.12.11;
        Sat, 21 May 2005 09:12:12 -0700 (PDT)
Received-SPF: neutral (some-domain.com: 000.000.000.000 is neither permitted nor
denied by best guess record for domain of [e-mail])
Received: from user-0c0sxxf.ddddd.tttttttttt.com ([00.000.00.000])
	by pop-a000c00.aaa.bb.mmmmmmmmm.net with esmtp (Exim 3.36 #10)
	id 0DOOaA-0006jU-00; Sat, 21 May 2005 09:12:10 -0700
Message-ID: <[e-mail]>
Date: Sat, 21 May 2005 12:11:47 -0400
From: Gary <[e-mail]>
User-Agent: Mozilla Thunderbird 1.0.2-1.3.3 (X11/20050513)
X-Accept-Language: en-us, en
MIME-Version: 1.0
To: Sharat <[e-mail]>
Subject: Sat's ?s on Thawte Notarization
X-Enigmail-Version: 0.91.0.0
Content-Type: multipart/mixed;
 boundary="------------000000000000000000000000"
Content-Disposition: attachment; filename="smime.p7m"
Content-Description: S/MIME Encrypted Message

This is a multi-part message in MIME format.
--------------000000000000000000000000
Content-Type: application/x-pkcs7-mime
Content-Transfer-Encoding: 7bit


--------------000000000000000000000000
Content-Type: application/x-pkcs7-mime;
 name="smime.p7m"
Content-Transfer-Encoding: base64
Content-Disposition: inline;
 filename="smime.p7m"

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--------------000000000000000000000000--

Comment 3

[Frank Wein [:mcsmurf]]

Ok, i have an /idea/ what might be happening here: It doesn't add a
X-Account-Key Header to the imported mails and so it doesn't know which
account/certificate the mails belong to.
BTW: Do you see a broken key sign when viewing such a mail (on the right with
Normal Header View)?

Comment 4

[SS]

(In reply to comment #3)
> Ok, i have an /idea/ what might be happening here: It doesn't add a
> X-Account-Key Header to the imported mails and so it doesn't know which
> account/certificate the mails belong to.
> BTW: Do you see a broken key sign when viewing such a mail (on the right with
> Normal Header View)?

Well that doesn't help my cause ... like I said I was planning on getting away
from Microsoft Outlook.  At any rate I'm glad I uninstall Outlook nor delete all
the emails.

In the newer emails I see both a sign pen (indicates digital signature) and a
key (indicating encryption).  The ones that I imported from outlook has neither
the sign pen nor the key.

Thanks!

Comment 5

[Frank Wein [:mcsmurf]]

Ok, new idea (btw: you don't have to comment on this :), this is just for other
developers): If i import signed&encrypted mails from OE, it works here (so not
related to x-account-key). I rather think this is a problem of the mail format,
OE uses Content-Type:
application/x-pkcs7-mime;smime-type=enveloped-data;boundary="----=_NextPart_000_0026_01C56E7E.62D49200";name="smime.p7m"
and just one single part. But the example mail here from Outlook uses
Content-Type: multipart/mixed;boundary="------------000000000000000000000000"
and includes two parts (one empty and one with the encrypted content).

Comment 6

[Frank Wein [:mcsmurf]]

BTW: Someone else just sent me a signed mail with Outlook 2003 and it just
worked fine. Maybe that Yahoo does some MIME magic also broke something here
(with the test mail you sent me)?

Comment 7

[SS]

(In reply to comment #6)
> BTW: Someone else just sent me a signed mail with Outlook 2003 and it just
> worked fine. Maybe that Yahoo does some MIME magic also broke something here
> (with the test mail you sent me)?

It seems like we are getting a little off the track here ... the problem is 
not with receiving emails when sent from Outlook and being received by 
Thunderbird.  The problem is when one decides to use Thunderbird as a primary 
client and imports all emails, settings, certificates, etcetera all the 
singned and encrypted emails are blank.  These emails are still viewable in 
Outlook.  Just a point I want to make is that all new emails sent and received 
with Thunderbird as a primary client are just fine and there are no S&E 
issues.  It is only the ones that were IMPORTED!

Comment 8

[Gervase Markham [:gerv]]

This is an automated message, with ID "auto-resolve01".

This bug has had no comments for a long time. Statistically, we have found that
bug reports that have not been confirmed by a second user after three months are
highly unlikely to be the source of a fix to the code.

While your input is very important to us, our resources are limited and so we
are asking for your help in focussing our efforts. If you can still reproduce
this problem in the latest version of the product (see below for how to obtain a
copy) or, for feature requests, if it's not present in the latest version and
you still believe we should implement it, please visit the URL of this bug
(given at the top of this mail) and add a comment to that effect, giving more
reproduction information if you have it.

If it is not a problem any longer, you need take no action. If this bug is not
changed in any way in the next two weeks, it will be automatically resolved.
Thank you for your help in this matter.

The latest beta releases can be obtained from:
Firefox:     http://www.mozilla.org/projects/firefox/
Thunderbird: http://www.mozilla.org/products/thunderbird/releases/1.5beta1.html
Seamonkey:   http://www.mozilla.org/projects/seamonkey/

Comment 9

[Gervase Markham [:gerv]]

This bug has been automatically resolved after a period of inactivity (see above
comment). If anyone thinks this is incorrect, they should feel free to reopen it.

Comment 10

[Ian Stokes-Rees]

I think the source of this bug is still there.  I get blank emails in Thunderbird 1.5.0.10 under FC5 when they are signed by an X509 certificate even if the certificate is loaded.  One wrinkle: they appear to be blank if the messages have been sent to a mailing list, so presumably the mailing list will alter some of the headers and possibly the body.  I have attached one such example.  I think this bug is related to bug 315170, and I'm going to search for others.

Comment 11

[Ian Stokes-Rees]

Attachment: Example of email which appears blank in Thunderbird

Comment 12

[Wayne Mery (:wsmwk)]

  Ian Stokes-Rees, thanks for the update. Can you reproduce the problem using a current beta version?  found at http://www.mozillamessaging.com/en-US/thunderbird/early_releases/ .... backup your profile first and you'll need a matching version for enigmail

Comment 13

[[:Aureliano Buendía]]

I can confirm this issue also in latest beta release.

I think not is an enigmail issue related, because when I disable enigmail , TB show the same blank window.

ps: Ludo component Migration it is right?

Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.1.5pre) Gecko/20091009 Lightning/1.0pre Shredder/3.0pre ID:20091009032155

Comment 14

[Ludovic Hirlimann [:Usul]]

(In reply to comment #13)
> I can confirm this issue also in latest beta release.
> 
> I think not is an enigmail issue related, because when I disable enigmail , TB
> show the same blank window.

I think so too as the issue seems with cert signed emails.
 
> ps: Ludo component Migration it is right?

yeah but for more visibility security is better.

Comment 15

[[:Aureliano Buendía]]

Playing with attached testcase Error Console show an enigmail issue:

Warning: reference to undefined property mimeMsg.headers[headerName]
Source File: chrome://enigmail/content/enigmailMessengerOverlay.js
Line: 527

Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.1.6pre) Gecko/20091106 Lightning/1.0pre Shredder/3.0pre ID:20091106031950

Enigmail version 0.97b (20091105-0557)

Comment 16

[Patrick Brunschwig]

This looks like a bug in Enigmail (weird, I thought had fixed this).

Comment 17

[Ludovic Hirlimann [:Usul]]

(In reply to comment #16)
> This looks like a bug in Enigmail (weird, I thought had fixed this).

Do you want us to file in enigmail's bugzilla ?

Comment 18

[Patrick Brunschwig]

no, don't worry. I can fix bugs from here as well :-)

Comment 19

[Patrick Brunschwig]

I have tried to view the message attached to this bug with Safe Mode (i.e. all extensions disabled) -- I don't obtain anything at all. The error console is empty with or without Enigmail installed. So I don't think that this is really an Enigmail bug. Furthermore, I can't reproduce the error message with Enigmail enabled.

Mozilla/5.0 (X11; U; Linux i686; en-US; rv:1.9.1.6pre) Gecko/20091107 Shredder/3.0pre

Comment 20

[[:Aureliano Buendía]]

(In reply to comment #0)
> User-Agent:       Mozilla/4.0 (compatible; MSIE 6.0; Windows NT 5.1; SV1; .NET
> CLR 1.1.4322)
> Build Identifier: "Thunderbird/1.0.2"
> 
> After a lot of reluctance I have just downloaded "Thunderbird 1.0.2".  In 
> addition I also have "Enigmail" so I can use my OpenPGP encryption.  I have 
> recently imported all my messages from "Outlook 2003".  

:-\
but probably Patrick is right and this issue is a dupe of bug #315170. Or not?

Comment 21

[[:Aureliano Buendía]]

Reading better comment #0 I think that title of this issue is wrong: this bug is closely dupe of bug #315170 and not is related to enigmail.

Feel free to reopen if I'm wrong.

ps: user confuse enigmail action with Thawte certificate, it seems.

Comment 22

[Patrick Brunschwig]

I have analyzed the attached message. This has nothing to do with importing emails from outlook, but simply with the fact that the message structure is invalid.

The message is a S/MIME signed messages, which needs to have a well-defined structure:
- header
- S/MIME signed message following the rules of RFC 822

However, the attached example has the following structure:
- header
- S/MIME signed message following the rules of RFC 822
- another MIME part

Thunderbird does not decrypt/verify such a message, which I think is acceptable.