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Thunderbird + Enigmail + saving draft with encryption

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  Thunderbird + Enigmail + saving draft with encryption Paul Sutton <zleap@disroot.org> - 2019-02-01 19:30 +0100
    Re: Thunderbird + Enigmail + saving draft with encryption Étienne Mollier <etienne.mollier@mailoo.org> - 2019-02-01 22:30 +0100
      Re: Thunderbird + Enigmail + saving draft with encryption Paul Sutton <zleap@disroot.org> - 2019-02-01 22:50 +0100
    Re: Thunderbird + Enigmail + saving draft with encryption didier gaumet <didier.gaumet@gmail.com> - 2019-02-02 10:20 +0100
      Re: Thunderbird + Enigmail + saving draft with encryption Paul Sutton <zleap@disroot.org> - 2019-02-02 14:20 +0100
        Re: Thunderbird + Enigmail + saving draft with encryption Paul Sutton <zleap@disroot.org> - 2019-02-02 14:30 +0100
          Re: Thunderbird + Enigmail + saving draft with encryption didier gaumet <didier.gaumet@gmail.com> - 2019-02-03 10:00 +0100
            Re: Thunderbird + Enigmail + saving draft with encryption Étienne Mollier <etienne.mollier@mailoo.org> - 2019-02-03 13:30 +0100
    Re: Thunderbird + Enigmail + saving draft with encryption Thomas D Dial <tdial@acm.org> - 2019-02-02 20:30 +0100
      Re: Thunderbird + Enigmail + saving draft with encryption Cindy-Sue Causey <butterflybytes@gmail.com> - 2019-02-02 21:10 +0100
        Re: Thunderbird + Enigmail + saving draft with encryption Paul Sutton <zleap@disroot.org> - 2019-02-02 21:30 +0100

#204907 — Thunderbird + Enigmail + saving draft with encryption

-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

Hi

Thunderbird + Enigmail has an option in "account settings" OpenPGP
Security to save a draft of a message with encryption, as expected this
saves the draft but with a new subject as "Encrypted message" and it
appears in drafts as this.

If you save the message,  close the compose window,  then go to Drafts, 
then reopen the message for more editing before sending the subject
remains as "Encrypted message" and you lose the original subject header.

I just wondered if this is what is meant to happen ? or is the original
subject header supposed to be restored.  Has anyone else noticed this.

System information

Thunderbird 60.4.0 (64-bit)

Enigmail 2.0.9

Distributor ID:    Debian
Description:    Debian GNU/Linux 9.7 (stretch)
Release:    9.7
Codename:    stretch
psutton@zleap:~$

Linux zleap 4.9.0-8-amd64 #1 SMP Debian 4.9.130-2 (2018-10-27) x86_64
GNU/Linux


Paul Sutton




- -- 
Paul Sutton
http://www.zleap.net
https://www.linkedin.com/in/zleap/
gnupg : 7D6D B682 F351 8D08 1893  1E16 F086 5537 D066 302D
-----BEGIN PGP SIGNATURE-----
Comment: Using GnuPG with Thunderbird - https://www.enigmail.net/

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#204911

On 2/1/19 7:26 PM, Paul Sutton wrote:
> If you save the message,  close the compose window,  then go to Drafts, 
> then reopen the message for more editing before sending the subject
> remains as "Encrypted message" and you lose the original subject header.
> 
> I just wondered if this is what is meant to happen ? or is the original
> subject header supposed to be restored.  Has anyone else noticed this.
Good Day Paul,

Yep, sounds to me that it is a feature to avoid leaking your email's
metadata.  Whom discusses with who and on which topic is an
interesting information indeed, even without being able to decipher
what's inside the fold.

Not sure if it's worth the pain though, since mail servers use these
metadata to properly route your email anyway; but I may have missed
interesting novelties on autocrypt side.

Cheers,
-- 
Étienne Mollier <etienne.mollier@mailoo.org>

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#204912

[Multipart message — attachments visible in raw view] — view raw

On 01/02/2019 21:24, Étienne Mollier wrote:
> On 2/1/19 7:26 PM, Paul Sutton wrote:
>> If you save the message,  close the compose window,  then go to Drafts, 
>> then reopen the message for more editing before sending the subject
>> remains as "Encrypted message" and you lose the original subject header.
>>
>> I just wondered if this is what is meant to happen ? or is the original
>> subject header supposed to be restored.  Has anyone else noticed this.
> Good Day Paul,
>
> Yep, sounds to me that it is a feature to avoid leaking your email's
> metadata.  Whom discusses with who and on which topic is an
> interesting information indeed, even without being able to decipher
> what's inside the fold.
>
> Not sure if it's worth the pain though, since mail servers use these
> metadata to properly route your email anyway; but I may have missed
> interesting novelties on autocrypt side.
>
> Cheers,

I will disable it for now, if anyone else notices this,  then perhaps it
is something that needs to be reported as a bug,  I would expect the
original subject to be restored, or failing that TB could simply append
the subject in some way.   It is interesting when you're drafts folder
is full of e-mails with the header "Encrypted message" unless you can
remember what time you saved the message finding a specific message is
impossible.

I think the idea is that as messages on say an IMAP server are stored on
that remote mail server any messages in draft are also stored there,  so
saving a message would leave the e-mail in plain text,  while the
messages in sent and inbox would be encrypted.  So encrypting drafts
make sense.l

Useful feature in a way but not that useful in the current
implementation. so as you said not worth it.

If we can confirm this it may be worth looking at sending in a bug report.

Paul

-- 
Paul Sutton
http://www.zleap.net
https://www.linkedin.com/in/zleap/
gnupg : 7D6D B682 F351 8D08 1893  1E16 F086 5537 D066 302D

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#204916

Hello Paul,

Same versions of thunderbird and Enigmail here but Debian Buster.

I do not observe the same thing as you do: the draft is saved with the
intended title

It is probably of no importance but my Debian (and Thunderbird) is in french

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#204922

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On 02/02/2019 09:14, didier gaumet wrote:
> Hello Paul,
>
> Same versions of thunderbird and Enigmail here but Debian Buster.
>
> I do not observe the same thing as you do: the draft is saved with the
> intended title
>
> It is probably of no importance but my Debian (and Thunderbird) is in french

Hi didier

That perhaps suggests the issue is with my set up somewhere,  or it is
fixed in either the French version or Buster.   It may be due to another
package which is causing the issue.

A copy of this e-mail is now in my drafts as "Encrypted Message", but
appears in the compose as it should be.

Lets keep an eye on it via the list. 

Thanks

Paul

-- 
Paul Sutton
http://www.zleap.net
https://www.linkedin.com/in/zleap/
gnupg : 7D6D B682 F351 8D08 1893  1E16 F086 5537 D066 302D

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#204923

[Multipart message — attachments visible in raw view] — view raw

On 02/02/2019 13:12, Paul Sutton wrote:
> On 02/02/2019 09:14, didier gaumet wrote:
>> Hello Paul,
>>
>> Same versions of thunderbird and Enigmail here but Debian Buster.
>>
>> I do not observe the same thing as you do: the draft is saved with the
>> intended title
>>
>> It is probably of no importance but my Debian (and Thunderbird) is in french
> Hi didier
>
> That perhaps suggests the issue is with my set up somewhere,  or it is
> fixed in either the French version or Buster.   It may be due to another
> package which is causing the issue.
>
> A copy of this e-mail is now in my drafts as "Encrypted Message", but
> appears in the compose as it should be.
>
> Lets keep an eye on it via the list. 
>
> Thanks
>
> Paul
>
So yes, steps i take are as follows:

With that option enabled,  (encrypt message in drafts folder)

Create new e-mail

Enter subject header

 Save (so that the message is stored in to drafts)

Check drafts folder to see what the message is named

close tb and message compose window(s)

Re open TB,  click Drafts,  edit message, (it will be in there as
Encrypted Message)

Rather than the message reverting to back the original subject header
you entered earlier it is now Encrypted Message,

so Manually edit

This happens on two computers,  netbook and Desktop both running Debian
9.7 (non free) with updates applied.  

Paul

1-- 
Paul Sutton
http://www.zleap.net
https://www.linkedin.com/in/zleap/
gnupg : 7D6D B682 F351 8D08 1893  1E16 F086 5537 D066 302D

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#204944

In my previous test I did not close Thunderbird before reopening the
signed and encrypted draft message.
this time I did it and nothing changed: The right title of the draft was
still there.

I prefer to stick to Stable but my main laptop is fairly new, that is
why Buster is installed on it.

So on a previous laptop, french Debian Stable with all updates
installed, with contrib, non-free; proposed-updates, updates,
security-updates, backports enable (but no backport package installed)

Same test and same result as with Buster on my new laptop: the title is
correctly saved and correctly sent after reopening Thunderbird.

In case it could be significant:
- I use Gnome desktop environment (if you use a lighter DE or a WM it
would be possible that a library that improves Thunderbird/Enigmail (but
is neither considered recommand or suggest) is not installed.
- I used my gmail address, so it's an IMAP remote storage of the draft.

Sorry, I have no other clue...

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#204953

Dider Gaumet, on 2019-02-03 :
> In my previous test I did not close Thunderbird before reopening the
> signed and encrypted draft message.
> this time I did it and nothing changed: The right title of the draft was
> still there.

Good Day,

It could have been temporary, I've seen these symptoms some time
last week perhaps, but haven't reproduced the phenomenon since
then, on my side.  My Thunderbird version is now 60.5 for few
days, on Sid channel.  Might have been related...

My drafts are usually written down with vi, so not much use of
the Draft/ IMAP folder here, actually.  :^)

Kind Regards,
-- 
Étienne Mollier <etienne.mollier@mailoo.org>

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#204930

On Fri, 2019-02-01 at 18:26 +0000, Paul Sutton wrote:
> Hi
> 
> Thunderbird + Enigmail has an option in "account settings" OpenPGP
> Security to save a draft of a message with encryption, as expected
> this
> saves the draft but with a new subject as "Encrypted message" and it
> appears in drafts as this.
> 
> If you save the message,  close the compose window,  then go to
> Drafts, 
> then reopen the message for more editing before sending the subject
> remains as "Encrypted message" and you lose the original subject
> header.
> 
> I just wondered if this is what is meant to happen ? or is the
> original
> subject header supposed to be restored.  Has anyone else noticed this.

I noticed this a few weeks or a month ago and took it to be a somewhat
inelegant, maybe incompletely implemented, feature intended to improve
metadata security. I believe "Encrypted message" also becomes the
subject of the transmitted message. 

Exposure of the  metadata showing who is in contact with whom, and when,
is pretty much inescapable, but the subject line, which is not
encrypted, also can  provide useful information to an eavesdropper, even
if she cannot decrypt the message body. This is noted in some PGP or GPG
documentation I have seen, accompanied by recommendations to obscure the
Subject: line and put the true subject within the body.

Tom Dial
> 
> System information
> 
> Thunderbird 60.4.0 (64-bit)
> 
> Enigmail 2.0.9
> 
> Distributor ID:    Debian
> Description:    Debian GNU/Linux 9.7 (stretch)
> Release:    9.7
> Codename:    stretch
> psutton@zleap:~$
> 
> Linux zleap 4.9.0-8-amd64 #1 SMP Debian 4.9.130-2 (2018-10-27) x86_64
> GNU/Linux
> 
> 
> Paul Sutton
> 
> 
> 
> 

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#204931

On 2/2/19, Thomas D Dial <tdial@acm.org> wrote:
> I noticed this a few weeks or a month ago and took it to be a somewhat
> inelegant, maybe incompletely implemented, feature intended to improve
> metadata security. I believe "Encrypted message" also becomes the
> subject of the transmitted message.
>
> Exposure of the  metadata showing who is in contact with whom, and when,
> is pretty much inescapable, but the subject line, which is not
> encrypted, also can  provide useful information to an eavesdropper, even
> if she cannot decrypt the message body. This is noted in some PGP or GPG
> documentation I have seen, accompanied by recommendations to obscure the
> Subject: line and put the true subject within the body.


That's what I was thinking as I read this thread. That's a perfect
spot for it... right at the top of the email's main content/body where
it then sits ready for a quick copy-cut-paste when the time's
appropriate.

It would be like how at least some of us temporarily save intended
recipient email addresses in that same spot while saving draft email
copies. That's an old netiquette type trick so that things fail in the
event we accidentally click "Send" instead of "Save Draft" or their
equivalents across email clients. :)

That part I read about how subject lines all look the same once
encrypted > GACK! It sounds like there's room for a wishlist bug
report about an option to somehow save a tickler of a reminder instead
of the real subject. A key as to the meaning of that tickler could
then be saved elsewhere, e.g. as a handwritten note, in the same way
passwords are occasionally saved on scraps of paper scattered
everywhere. :)

Cindy :)
-- 
Cindy-Sue Causey
Talking Rock, Pickens County, Georgia, USA

* runs with birdseed *

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#204932

-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256


On 02/02/2019 20:08, Cindy-Sue Causey wrote:
> On 2/2/19, Thomas D Dial <tdial@acm.org> wrote: >> I noticed this a few weeks or a month ago and took it to be a
somewhat >> inelegant, maybe incompletely implemented, feature intended
to improve >> metadata security. I believe "Encrypted message" also
becomes the >> subject of the transmitted message. >> >> Exposure of the
metadata showing who is in contact with whom, and when, >> is pretty
much inescapable, but the subject line, which is not >> encrypted, also
can provide useful information to an eavesdropper, even >> if she cannot
decrypt the message body. This is noted in some PGP or GPG >>
documentation I have seen, accompanied by recommendations to obscure the
>> Subject: line and put the true subject within the body. > > > That's
what I was thinking as I read this thread. That's a perfect > spot for
it... right at the top of the email's main content/body where > it then
sits ready for a quick copy-cut-paste when the time's > appropriate. > >
It would be like how at least some of us temporarily save intended >
recipient email addresses in that same spot while saving draft email >
copies. That's an old netiquette type trick so that things fail in the >
event we accidentally click "Send" instead of "Save Draft" or their >
equivalents across email clients. :) > > That part I read about how
subject lines all look the same once > encrypted > GACK! It sounds like
there's room for a wishlist bug > report about an option to somehow save
a tickler of a reminder instead > of the real subject. A key as to the
meaning of that tickler could > then be saved elsewhere, e.g. as a
handwritten note, in the same way > passwords are occasionally saved on
scraps of paper scattered > everywhere. :) > > Cindy :)
Having the subject header copied to the top of the message body sounds
like a good idea.  I can do that manually but having software do that
could be helpful to people too.

A wish list seems a good idea too,  anything to help improve software is
a good thing.

regards

Paul :)



Paul

- -- 
Paul Sutton
http://www.zleap.net
https://www.linkedin.com/in/zleap/
gnupg : 7D6D B682 F351 8D08 1893  1E16 F086 5537 D066 302D
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