Re: [Enigmail] Enigmail Toolbar

2015-03-28 Thread Olav Seyfarth
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

Hi Mike,

I think that INLINE/MIME, signed/unsigned and blank subject should not depend
on each other. That is, having one set or not should not yield other results for
another. Users would not expect this (and rather manually set it).

 We would not want to present Aunt Sally with the empty subject line.

It might be worth considering to make this warning optional and switch it off
by default indeed.

 If using PGP it makes sense to set PGP/MIME.

If a message is neither signed nor encrypted by Enigmail, PGP/MIME ist not used
even if it's set or default. Usual MIME is used then for HTML mails, and plain
for plain text mails.

Olav
- -- 
The Enigmail Project - OpenPGP Email Security For Mozilla Applications
-BEGIN PGP SIGNATURE-
Version: GnuPG v2
Comment: Dies ist eine elektronische Signatur - http://www.enigmail.net/

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=BBL4
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Re: [Enigmail] Subject line warnings

2015-03-28 Thread Doug Barton

On 3/28/15 6:31 AM, Mike Acker wrote:

On 03/28/2015 07:21 AM, Ron OHara wrote:

Hi,

In Thunderbird, you are warned if you send an email with a blank
Subject.If the message is to be encrypted, best practice is to NOT
have a Subject line.  The Subject line is not encrypted and thus 'leaks'
information.

Any ideas on how to:
1 - suppress the Thunderbird warning if Subject is blank and the mail is
encrypted
2 - issue a warning (from Enigmail?) if the Subject is NOT blank, and
the mail is encrypted.

Regards
Ron OHara



just enter a dummy subject line, e.g. March Madness

you are fussing over an un-important point: you cannot avoid traffic
analysis unless you toss your smart-phone in the dumpster and ride your
bike.


+1


--
I am conducting an experiment in the efficacy of PGP/MIME signatures. 
This message should be signed. If it is not, or the signature does not 
validate, please let me know how you received this message (direct, or 
to a list) and the mail software you use. Thanks!




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Re: [Enigmail] Enigmail Toolbar

2015-03-28 Thread Doug Barton
When starting a new topic please don't reply to a message on the list 
and change the subject line. Doing so causes your new topic to show 
under the previous one for those using mail readers that thread 
properly, and may cause your message to be missed altogether if someone 
has blocked that thread.


Instead, please save the list address to your address book and then 
start a completely new message.


hope this helps,

Doug

--
I am conducting an experiment in the efficacy of PGP/MIME signatures. 
This message should be signed. If it is not, or the signature does not 
validate, please let me know how you received this message (direct, or 
to a list) and the mail software you use. Thanks!




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[Enigmail] Enigmail Toolbar

2015-03-28 Thread Mike Acker
Olav,--

Thank you for your very thoughtful reply.  The point of issue that
prompted me to write arose when I attempted to sign a message I had
written regarding blank subject lines.   As soon as I attempted to sign
the message I was warned that my message was being converted to plain
text,-- which I did not want.   So, I started hunting for the PGP/MIME
switch.   I found it and set it to use PGP/MIME

But let's talk about Aunt Sally: we would not want to present her with
that message, either.   So we are really between a rock and a hard spot
in this.My feeling is that if I'm going to use PGP it is because I
expect the recipient is also using PGP.   That being the case it makes
sense to me to set PGP/MIME as the default -- whenever either\or
encryption|signature is selected.   I notice for this message I have to
re-select the PGP/MIME option.

let me know what you think!

I think a huge part of our problem these days is to get people to quit
fussing over 2-factor authentications and start worrying about digital
authentications of documents, generally

=

On 03/28/2015 01:02 PM, Olav Seyfarth wrote:
 Hi Mike,

  there should be 3 selections: Encryption, Signing, and PGP/MIME

 I disagree. Aunt Sally will ONLY care about encrypt or not. More
 learned folks
 may want to change their default signing setting for specific
 messages. But only
 nerds care to switch INLINE/MIME. I'm not trying to offend you, just
 making one
 point clear: Enigmail must be as usable for anyone. And MOST people
 will be
 confused by a INLINE/MIME selection.

 For the expert/nerd: the Label Enigmail: in that button bar is
 clickable and
 you may set INLINE/MIME there. I do agree that this is not good UI
 design since
 users are not to expect Labels to be clickable. It's what it is for
 now. We may
 come up with a better solution. If Patrick does a INLINE/MIME button,
 then I
 urge to hide it per default. Experts may then drag it into their
 perferred pos.

 Apart from the UI: The next Enigmail version we set PGP/MIME as default.

 Olav

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-- 
/Mike



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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

--
I am conducting an experiment in the efficacy of PGP/MIME signatures. 
This message should be signed. If it is not, or the signature does not 
validate, please let me know how you received this message (direct, or 
to a list) and the mail software you use. Thanks!





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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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This message should be signed. If it is not, or the signature does not 
validate, please let me know how you received this message (direct, or 
to a list) and the mail software you use. Thanks!




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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

-- 
OpenPGP / GPG key: 0x14B7E62420E51038
I encrypt emails with GPG, Thunderbird  Enigmail.




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[Enigmail] Subject line warnings

2015-03-28 Thread Mike Acker
On 03/28/2015 07:21 AM, Ron OHara wrote:
 Hi,

 In Thunderbird, you are warned if you send an email with a blank
 Subject.If the message is to be encrypted, best practice is to NOT
 have a Subject line.  The Subject line is not encrypted and thus 'leaks'
 information.

 Any ideas on how to:
 1 - suppress the Thunderbird warning if Subject is blank and the mail is
 encrypted
 2 - issue a warning (from Enigmail?) if the Subject is NOT blank, and
 the mail is encrypted.

 Regards
 Ron OHara


just enter a dummy subject line, e.g. March Madness

you are fussing over an un-important point: you cannot avoid traffic
analysis unless you toss your smart-phone in the dumpster and ride your
bike.

-- 
/Mike

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[Enigmail] Subject line warnings

2015-03-28 Thread Ron OHara
Hi,

In Thunderbird, you are warned if you send an email with a blank
Subject.If the message is to be encrypted, best practice is to NOT
have a Subject line.  The Subject line is not encrypted and thus 'leaks'
information.

Any ideas on how to:
1 - suppress the Thunderbird warning if Subject is blank and the mail is
encrypted
2 - issue a warning (from Enigmail?) if the Subject is NOT blank, and
the mail is encrypted.

Regards
Ron OHara


-- 
public identify: https://www.onename.io/ron_ohara

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[Enigmail] Enigmail Toolbar

2015-03-28 Thread Mike Acker
I see they revised the Enigmail Toolbar.   are they taking lessons from
Julie Larson-Green ;) ?

anyway, there should be 3 selections: Encryption, Signing, and
PGP/MIME.Generally if you are just signing a message or actually
encrypting and signing -- you want to use PGP/MIME.   I would then put
an option on the Toolbar for PGP/MIME and have it switch on
automatically if either the Encryption and|or the signing option is
selected, allowing the user to manually switch it off -- which would
then force plaintext formatting.

-- 
/Mike




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[Enigmail] Enigmail - gpg-agent - TTL

2015-03-28 Thread Blaise Pascal
Hi,

using Linux Mint 17 / Thunderbird (24.4.0) / Enigmail 17.2 with gpg2...
Once deciphered, Enigmail (or gpg-agent) keeps the passphrase forever in
memory although I have a .gnupg/gpg-agent.conf containing:

max-cache-ttl 15
default-cache-ttl 15

I'm not sure that gpg-agent.conf is correctly read when Enigmail initiates
gpg-agent at the pop-up of the pinentry windows.

HUP , killall, ..etc does not help.

Should I try to configure gpg-agent manually with gpgconf ?

Any ideas ?

Thanks
BP


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Re: [Enigmail] Enigmail - gpg-agent - TTL

2015-03-28 Thread Patrick Brunschwig
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

On 28.03.15 15:59, Blaise Pascal wrote:
 Hi,
 
 using Linux Mint 17 / Thunderbird (24.4.0) / Enigmail 17.2 with
 gpg2... Once deciphered, Enigmail (or gpg-agent) keeps the
 passphrase forever in memory although I have a
 .gnupg/gpg-agent.conf containing:
 
 max-cache-ttl 15 default-cache-ttl 15

The ttl is in seconds ... 15 seconds seems quite short to me ;-)

 I'm not sure that gpg-agent.conf is correctly read when Enigmail
 initiates gpg-agent at the pop-up of the pinentry windows.
 
 HUP , killall, ..etc does not help.
 
 Should I try to configure gpg-agent manually with gpgconf ?
 
 Any ideas ?

I wonder if gpg-agent is used at all. Many distributions are set up
such that a different tool for caching your passphrase is used (e.g.
gnome-keyring).

- -Patrick


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Version: GnuPG v2

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Re: [Enigmail] Enigmail Toolbar

2015-03-28 Thread Olav Seyfarth
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

Hi Mike,

 there should be 3 selections: Encryption, Signing, and PGP/MIME

I disagree. Aunt Sally will ONLY care about encrypt or not. More learned folks
may want to change their default signing setting for specific messages. But only
nerds care to switch INLINE/MIME. I'm not trying to offend you, just making one
point clear: Enigmail must be as usable for anyone. And MOST people will be
confused by a INLINE/MIME selection.

For the expert/nerd: the Label Enigmail: in that button bar is clickable and
you may set INLINE/MIME there. I do agree that this is not good UI design since
users are not to expect Labels to be clickable. It's what it is for now. We may
come up with a better solution. If Patrick does a INLINE/MIME button, then I
urge to hide it per default. Experts may then drag it into their perferred pos.

Apart from the UI: The next Enigmail version we set PGP/MIME as default.

Olav
- -- 
The Enigmail Project - OpenPGP Email Security For Mozilla Applications
-BEGIN PGP SIGNATURE-
Version: GnuPG v2
Comment: Dies ist eine elektronische Signatur - http://www.enigmail.net/

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-END PGP SIGNATURE-

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