Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-04-05 Thread Ben McGinnes
On 29/03/2015 9:47 am, Jérôme Pinguet wrote:
 
 By the way Daniel, thanks for your GPG best practices page and more
 generally for your work related to GPG, Riseup and Debian! :-) I
 often refer to Riseup GPG Best practices during the cryptoparties I
 organize in Marseille.

Great to hear that at least somewhere in the world people are still
running cryptoparties like two and a half years ago (in spite of the
quite vicious attack on Asher by certain misogynistic hacker types in
a certain European computing club).  So though we don't run them
ourselves anymore, or at least for the moment, we're always very
pleased to hear that the original idea is not dead.  Cheers!  :)


Regards,
Ben



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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-04-05 Thread Ben McGinnes
On 5/04/2015 11:50 pm, Patrick Brunschwig wrote:
 On 05.04.15 15:41, Ben McGinnes wrote:
 
 However, if you're in real trouble from this, the version of
 pinentry and gpg-agent I have running with GPG 2.1.2 include a
 little tick box which allows the passphrase to be visible when you
 type it in.  I don't use it myself, but no doubt others will.
 Presumably you can't see that and I assume it is gpg-agent itself
 (bundled with the GnuPG release) rather than pinentry, which is the
 same library for both 2.0 and 2.1.
 
 That's the special version of pinentry for Mac OS X only. pinentry-mac
 is not part of the official GnuPG toolchain but maintained separately.
 
 The versions for Windows and Linux (which are provided by GnuPG) don't
 have this feature.

Interesting, I hadn't realised that.  Especially since I'm not using
GPGTools, though that is tucked away in its own little directory,
safely out of the way of anything resembling my $PATH.  This whole
setup is a slightly customised compilation of the sources from
MacPorts and the gnupg-2.1.2 tarball's checksum matched the one I
originally downloaded from gnupg.org, hence assuming that it was the
same gpg-agent.  Since it isn't that might explain a few things, like
how I was finally able to get past those damned linker errors which
prevented compiling that other copy (and all its predecessors).

Well, I'm sure it will be more or less fine.  I only made the switch
now because somebody decided to drop support for 1.4 in Enigmail.  ;)

Anyway, I'm pretty sure that the only configuration detail I haven't
yet fully tracked down in the new system is getting proxies correctly
configured for accessing the keyservers (to avoid traffic analysis
under the new mandatory data retention laws here and potentially
reveal the identities of those I'm corresponding with).  If that can't
really be sorted out easily, though, I'll just add an SKS server after
I next upgrade my server and counter that sort of analysis with
everything.  It's only about 6.5Gb anyway.


Regards,
Ben



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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-04-05 Thread Ben McGinnes
On 26/03/2015 9:36 am, Andre Lahmann wrote:
 Ok, just for the record: this is an issue with pinentry - see e.g.
 https://bugs.launchpad.net/ubuntu/+source/pinentry/+bug/326132
 https://bugs.g10code.com/gnupg/issue1374
 https://bugs.g10code.com/gnupg/issue1368
 
 It's absolutely ridiculous how usability is screwed by design and
 justified with security reasons...

As Ludwig and Robert said, there are good reasons.

However, if you're in real trouble from this, the version of pinentry
and gpg-agent I have running with GPG 2.1.2 include a little tick box
which allows the passphrase to be visible when you type it in.  I
don't use it myself, but no doubt others will.  Presumably you can't
see that and I assume it is gpg-agent itself (bundled with the GnuPG
release) rather than pinentry, which is the same library for both 2.0
and 2.1.


Regards,
Ben



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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-29 Thread Anne Wilson
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 29/03/2015 10:32, Samir Nassar wrote:
 On Sunday, March 29, 2015 10:26:53 AM Anne Wilson wrote:
 Personally I prefer my password to be reference to a book - and
 you haven't a snowball in hell's chance of knowing which book or
 what reference to it :-)  I doubt if even my closest family would
 guess the book.
 
 You might be wrong, you might be right, at most you are right for
 the situation you live in.
 
 Part of the discussion happening here is about general principles
 that cover cases where the risk is assessed to be adversaries who
 are making trillion guesses per second.
 
I'm cautious, but not paranoid.  Since the result looks like a random
sequence it would not be easy to crack, and there are certainly easier
places for him to go.  However, I appreciate that in some
circumstances, for example corporate accounts, you may have to take
some additional precaution.  I do feel strongly, though, that the more
complicated something is, and the more steps it takes to complete
the entry, the more you increase the risk.

A personal opinion, though.

Anne

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Version: GnuPG v2
Comment: Using GnuPG with Thunderbird - http://www.enigmail.net/

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-29 Thread Philip Jackson
On 28/03/15 20:30, Daniel Kahn Gillmor wrote:
 I quite like the Keepass approach.
 
 But it's not clear to me that this will work, at least for the versions
 of pinentry i've seen that grab the input devices (i'm seeing this on
 X11, at any rate).  In this case, I don't think there is a way to
 trigger keepass to get it to type into the pinentry dialog.
 
 What platforms as this approach been tested on?

I used KeePass2 on WindowsXP and 7 for some years and the autotype with 2
channel obfuscation worked very well as did the selection and inclusion of the
various dialog boxes that would require auto-completion with either username and
password or just password according to the case.  This included the pinentry 
boxes.

KeePass2 wipes the clipboard after a delay which can be set by the user.

When I moved from Windows to UbuntuStudio 14.04, I tried KeePassX which was in
the distro as standard but it seemed to me more limited so I went back to
KeePass2 and had quite a bit of trouble to get the autotype working although the
KeePass website does have some info.  The difficulty was linked to the
dependence on mono.

It still doesn't work in the same easy fashion that I had with Windows7 and I
can't get a system wide keyboard shortcut for autotype to work at all.  Nor can
I get the KeePass2 shortcut of Ctrl-V to do the autotype but a rightclick
followed by a left click on the dropdown list does work ok.

(I noticed a Ubuntu software update a few days ago included some stuff on mono.
 Today, I have found that my keyboard numeric pad no longer works inside
KeePass2 and I'm wondering if the two events are connected.)

Philip



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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-29 Thread Samir Nassar
On Sunday, March 29, 2015 10:26:53 AM Anne Wilson wrote:
 Personally I prefer my
 password to be reference to a book - and you haven't a snowball in
 hell's chance of knowing which book or what reference to it :-)  I
 doubt if even my closest family would guess the book.

You might be wrong, you might be right, at most you are right for the 
situation you live in.

Part of the discussion happening here is about general principles that cover 
cases where the risk is assessed to be adversaries who are making trillion 
guesses per second.
 
Samir


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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-29 Thread Anne Wilson
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 28/03/2015 19:30, Daniel Kahn Gillmor wrote:
 I suppose the underlying question is whether you think the user's 
 OpenPGP passphrase is one of these strong passphrases that they
 should be able to remember, or whether you think it should be
 delegated to the mechanized password store

I don't believe a password needs to be either insanely long or too
complicated to remember.  Surely it only needs to be something
impossible to crack in a dictionary attack, yet based on something
memorable to you but unknown to others.  Personally I prefer my
password to be reference to a book - and you haven't a snowball in
hell's chance of knowing which book or what reference to it :-)  I
doubt if even my closest family would guess the book.

Anne
-BEGIN PGP SIGNATURE-
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Comment: Using GnuPG with Thunderbird - http://www.enigmail.net/

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-29 Thread Doug Barton

On 3/29/15 2:32 AM, Samir Nassar wrote:

On Sunday, March 29, 2015 10:26:53 AM Anne Wilson wrote:

Personally I prefer my
password to be reference to a book - and you haven't a snowball in
hell's chance of knowing which book or what reference to it :-)  I
doubt if even my closest family would guess the book.


You might be wrong, you might be right, at most you are right for the
situation you live in.

Part of the discussion happening here is about general principles that cover
cases where the risk is assessed to be adversaries who are making trillion
guesses per second.


Um, no, it really isn't. :)  The two components of your sentence 
general principles, and adversaries ... don't go together, at all.


Yes, there are some people who use PGP for serious, even potentially 
life-threatening purposes. Those people need really strong pass phrases, 
and perhaps even ones that are so long that they cannot be remembered, 
or typed easily.


But the vast majority of PGP users are doing it because it's fun, and 
have no need for that kind of drama. Is it nice to encourage good 
operational practices for pass phrases for the general type of user? 
Of course it is, and we should do that. But pretending that super-long, 
untypable pass phrases apply to anyone except an extreme few is just 
silliness.


But worse than it being ridiculous on its face, by pretending that these 
kinds of practices are, or should be commonplace it makes it harder for 
people how would like to learn about encryption to do so.


Doug

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-28 Thread Doug Barton

On 3/28/15 11:57 AM, Daniel Kahn Gillmor wrote:

If the only concern is leaving sensitive data in the clipboard after
use, maybe pinentry could*accept*  pastes, but then also clear the
clipboard after it was pasted into?


First, this discussion is moot because Werner won't change this.

Second, what you're describing isn't safe. Malware that watches the 
clipboard will still pick up what's pasted onto it, even if it gets 
cleared immediately after.


Finally, someone else already posted the right answer, a tool like 
Keepass can auto-type the password, bypassing the clipboard. It's also 
thought to be safe against key loggers, although there is some dispute 
on that topic.


I think that a case can be made for a better plan to be using a password 
that you can remember, and type. I would also argue that for most people 
there is no threat model that justifies a password so long that you 
can't remember or type it. :)


Doug

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-28 Thread Daniel Kahn Gillmor
[redirecting to gnupg-devel, setting mail-followup-to: there]

On Wed 2015-03-25 18:26:38 -0400, Robert J. Hansen wrote:
 My guess is that this is for added security.

 Correct.  Werner Koch has said several times that he will not change the
 code to permit CP into the dialog box, as that would leave sensitive
 data in your clipboard -- and the clipboard, by definition, can be read
 by any application, including malware.

If the only concern is leaving sensitive data in the clipboard after
use, maybe pinentry could *accept* pastes, but then also clear the
clipboard after it was pasted into?

I understand that this still encourages people to put their
passphrases into the clipboard, but that seems to be happening anyway.

What if, upon accepting a paste, pinentry was to expand the dialog a bit
and show a warning that says something like:

   Pasted!  Your clipboard has also been emptied, so that your
   passphrase isn't exposed to other applications.  GnuPG recommends
   never copying your passphrase to the clipboard.

  --dkg

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-28 Thread Doug Barton

On 3/28/15 12:30 PM, Daniel Kahn Gillmor wrote:

[so much for following up on gpg-devel; i'm replying to enigmail because
that's where this message went, even though i don't understand the
reason to keep this non-enigmail discussion here]

On Sat 2015-03-28 15:09:15 -0400, Doug Barton wrote:

Finally, someone else already posted the right answer, a tool like
Keepass can auto-type the password, bypassing the clipboard. It's also
thought to be safe against key loggers, although there is some dispute
on that topic.


I quite like the Keepass approach.

But it's not clear to me that this will work, at least for the versions
of pinentry i've seen that grab the input devices (i'm seeing this on
X11, at any rate).  In this case, I don't think there is a way to
trigger keepass to get it to type into the pinentry dialog.


Keepass has a way to specify the target window. But that method only 
works with certain types of dialogs. I just tried it with the Mac GPG 
Tools pinentry and it doesn't work. Of course there is no reason that 
the standard pinentry front ends couldn't be adjusted as needed.



What platforms as this approach been tested on?


Dunno. :)


I think that a case can be made for a better plan to be using a password
that you can remember, and type. I would also argue that for most people
there is no threat model that justifies a password so long that you
can't remember or type it. :)


I can sympathize with this sentiment.  In general, i think users should
keep a very small number of strong passphrases that they can remember
and can type, and should use the main one of those passprhases to
control a mechanized password store (like keepass) for all the rest of
them.

I suppose the underlying question is whether you think the user's
OpenPGP passphrase is one of these strong passphrases that they should
be able to remember, or whether you think it should be delegated to the
mechanized password store.


Yes, I agree with you in principle, and I do think that the secret key 
password is one that should be typeable.


And FWIW, one of the virtues of a secure key store like Keepass is that 
you can keep passwords in it whether you want to auto-type them or not. 
So if you have a strong password for something that you don't type 
often, you can keep it there to prompt your memory.


Doug

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-28 Thread Jérôme Pinguet
On 03/28/2015 08:30 PM, Daniel Kahn Gillmor wrote:
 [so much for following up on gpg-devel; i'm replying to enigmail because
 that's where this message went, even though i don't understand the
 reason to keep this non-enigmail discussion here]

 On Sat 2015-03-28 15:09:15 -0400, Doug Barton wrote:
 Finally, someone else already posted the right answer, a tool like 
 Keepass can auto-type the password, bypassing the clipboard. It's also 
 thought to be safe against key loggers, although there is some dispute 
 on that topic.
 I quite like the Keepass approach.

 But it's not clear to me that this will work, at least for the versions
 of pinentry i've seen that grab the input devices (i'm seeing this on
 X11, at any rate).  In this case, I don't think there is a way to
 trigger keepass to get it to type into the pinentry dialog.

 What platforms as this approach been tested on?
Debian Stable, KeePass2, pinentry-gtk-2 and pinentry-qt4 both work, and
are both a bit slow (it might take up to 30 seconds !!! for the pinentry
dialog to be accepted, but my password is not insanely long, it's in the
20-40 chars range). I tested it with both GnuPG 1.4.x and 2.0.x

In fact I use this on a daily basis combined with Enigmail. Sometimes,
for reasons beyond my grasp, pinentry complains of a wrong password.
When it happens, i restart keepass2 and then it works again. KeePass2
comes with tons of Mono packages and it's a bit sluggish, but I haven't
found anything as reliable yet in the limited offer of Debian packaged
free software password managers.

If the KeePass2-pinentry process was faster, it would be perfect.

By the way Daniel, thanks for your GPG best practices page and more
generally for your work related to GPG, Riseup and Debian! :-) I often
refer to Riseup GPG Best practices during the cryptoparties I organize
in Marseille.

Here is the link:
https://help.riseup.net/en/security/message-security/openpgp/best-practices

Jérôme

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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-26 Thread Ludwig Hügelschäfer
On 25.03.15 23:36, Andre Lahmann wrote:
 Ok, just for the record: this is an issue with pinentry - see e.g.
 https://bugs.launchpad.net/ubuntu/+source/pinentry/+bug/326132
 https://bugs.g10code.com/gnupg/issue1374
 https://bugs.g10code.com/gnupg/issue1368
 
 It's absolutely ridiculous how usability is screwed by design and
 justified with security reasons...

Please calm down. There is a good reason to not allow cp, see Roberts post.

After all, this is nothing Enigmail can change.

Ludwig




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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-25 Thread Robert J. Hansen
 My guess is that this is for added security.

Correct.  Werner Koch has said several times that he will not change the
code to permit CP into the dialog box, as that would leave sensitive
data in your clipboard -- and the clipboard, by definition, can be read
by any application, including malware.




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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-25 Thread Andre Lahmann
Ok, just for the record: this is an issue with pinentry - see e.g.
https://bugs.launchpad.net/ubuntu/+source/pinentry/+bug/326132
https://bugs.g10code.com/gnupg/issue1374
https://bugs.g10code.com/gnupg/issue1368

It's absolutely ridiculous how usability is screwed by design and
justified with security reasons...


Am 25.03.2015 um 22:55 schrieb Andre Lahmann:
 Hmm, I just tried it with GPGv1.4 but the pinentry dialogbox still
 does not allow copy and pasting... doesn't seem to be a GPGvX related
 issue or am I getting you wrong?
 
 Best,
 André
 
 Am 25.03.2015 um 22:44 schrieb mich...@yanovich.net:
 On 03/25/2015 05:40 PM, Andre Lahmann wrote:
 Hello,

 since upgrading to Enigmail 1.8.x it's not possible anymore to
 paste the passphrase into the pinentry dialogbox. I'm running
 Xubuntu 12.04 and neither ctrl+v nor mouse buffer is working (as
 I am managing my passphrases with keepass I also tried autotype
 without success). Is this a bug or a feature?!?

 Best, André

 This is a feature of GPGv2. I originally discovered this a few
 versions ago of Enigmail (probably 1.7.2). It seems that for GPGv2
 it requires specific applications for passphrase entry and of the
 ones that work with GPG none of them appear to allow
 copying/pasting of the passphrase, in my experience.

 My guess is that this is for added security.



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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-25 Thread Andre Lahmann
Hmm, I just tried it with GPGv1.4 but the pinentry dialogbox still
does not allow copy and pasting... doesn't seem to be a GPGvX related
issue or am I getting you wrong?

Best,
André

Am 25.03.2015 um 22:44 schrieb mich...@yanovich.net:
 On 03/25/2015 05:40 PM, Andre Lahmann wrote:
 Hello,
 
 since upgrading to Enigmail 1.8.x it's not possible anymore to
 paste the passphrase into the pinentry dialogbox. I'm running
 Xubuntu 12.04 and neither ctrl+v nor mouse buffer is working (as
 I am managing my passphrases with keepass I also tried autotype
 without success). Is this a bug or a feature?!?
 
 Best, André
 
 This is a feature of GPGv2. I originally discovered this a few
 versions ago of Enigmail (probably 1.7.2). It seems that for GPGv2
 it requires specific applications for passphrase entry and of the
 ones that work with GPG none of them appear to allow
 copying/pasting of the passphrase, in my experience.
 
 My guess is that this is for added security.
 
 
 
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Re: [Enigmail] Paste passphrase from clipboard into pinentry dialogbox

2015-03-25 Thread Jérôme Pinguet
On 03/25/2015 10:40 PM, Andre Lahmann wrote:
 Hello,

 since upgrading to Enigmail 1.8.x it's not possible anymore to paste the
 passphrase into the pinentry dialogbox. I'm running Xubuntu 12.04 and
 neither ctrl+v nor mouse buffer is working (as I am managing my
 passphrases with keepass I also tried autotype without success).
 Is this a bug or a feature?!?

 Best,
 André

Hi!

You could use keepass2 to type your password for you. In my experience
it's a bit slow if you have a very long password. The trick is to
increase default-cache-ttl in ~/.gnupg/gpg-agent.conf to improve usability.

Change default auto-type to {Password}{ENTER}, entering the name of the
target window helps (pinentry-gtk-2 or pinentry-qt4 for Debian Stable).

This method is not perfect: some malware could record virtual keystrokes
from keepass2. There is a Two-channel auto-type obfuscation feature
supposed to increase security but it doesn't work with pinentry-gtk-2 or
pinentry-qt4 AFAIK...

If anybody knows how to increase speed of keepas2 -- pinentry
communication or how to enable two-channel auto-type obfuscation, let me
know.

Enigmail 1.8.0 was terrible but 1.8.1 works very well on Debian Stable
with regular Icevode version. Thanks for the good work! :-)

Thanks.

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I encrypt emails with GPG, Thunderbird  Enigmail.
Please do the same or use my secure contact form: https://jerome.cc/gpg




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