Re: isolating the signature from encrypted data (was: sign encrypted emails)

2014-01-07 Thread MFPA
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA512

Hi


On Monday 6 January 2014 at 2:24:10 AM, in
mid:7677715.1slnlpw...@inno.berlin.laging.de, Hauke Laging wrote:



 That is correct. I am not aware of a possibility to get
 the data and the signature from GnuPG. But that doesn't
 mean it's not possible.

I think the thread you linked to [1] says it is possible using
GnuPG's --show-session-key and --override-session-key options. And at
the end of the thread, Werner says PGP/MIME signs and encrypts using
separate MIME containers, which makes it easy to strip off the
encryption layer.

[1] http://lists.gnupg.org/pipermail/gnupg-users/2004-April/022352.html

 Use both ways (one step, two steps) to sign and encrypt
 a file and have a look at the result with gpg
 --list-packets.

I did. Gpg --list-packets output starts the same. But to get all of
the info on the two-step signed then encrypted, I have to run gpg
- --list-packets again on the signed but not encrypted file to get the
info about the signature.


I also tried pgpdump, which gives the same information for the one
step and the two step files. It appears to be a different (and
smaller) set of information than gpg --list-packets generates.


- --
Best regards

MFPAmailto:expires2...@ymail.com

Live your life as though every day it was your last.
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Re: sign encrypted emails

2014-01-06 Thread Peter Lebbing
On 06/01/14 01:51, Hauke Laging wrote:
 Let me guess: Modifying the mail client so that it automatically removes 
 the word not would be illegitimate because for some strange reason 
 that would be solving social problems by technical means...

I guess it boils down to the point that I just don't see a use case.

I believe there are two scenario's you're treating:

- You wish to give significance to a mail being encrypted; this, for you,
changes the context of the contents. I disagree; I'd rather see it context-free
and unambiguous[1].

- You wish to catch noobs in the act when they forget to encrypt. I think secure
communications with noobs is impossible, so it doesn't help to plug a single
hole in the sieve[2].

The result is that I see no application for what you describe. At to that the
fact I find it a rather ugly kludge to sign a single message twice instead of
keeping all authenticated data inside the one signature, and you've lost me.

So I guess this discussion is indeed pretty much done.

HTH,

Peter.

[1] Hmmm, maybe we should define a formal e-mail language ;)
[2] I'm using noobs rather broadly here, since I think it takes a lot of
attention and rigour to secure communications.

-- 
I use the GNU Privacy Guard (GnuPG) in combination with Enigmail.
You can send me encrypted mail if you want some privacy.
My key is available at http://digitalbrains.com/2012/openpgp-key-peter

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Re: sign encrypted emails

2014-01-05 Thread Peter Lebbing
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On 05/01/14 04:38, Hauke Laging wrote:
 You are aware that is doesn't make any sense to make this claim without any
 argument after the opposite has been claimed with an argument (a very
 strong one)?

Eh? You yourself start this whole discussion by making the point that it is,
as things are now, unreliable to act differently depending on whether
encryption is applied to the message or not. That is precisely the whole
strong argument why people say: you just shouldn't act differently depending
on whether encryption is applied to the message or not.

I really do not understand one bit why you now say this is a claim without any
argument, I'm quite surprised. Unless you read without any argument as this
is a thing we agree on, but that requires bending the sentence beyond
breaking point ;).

I agree with Robert, you're trying to solve a social problem with a technical
solution.

HTH,

Peter.

- -- 
I use the GNU Privacy Guard (GnuPG) in combination with Enigmail.
You can send me encrypted mail if you want some privacy.
My key is available at http://digitalbrains.com/2012/openpgp-key-peter

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Re: sign encrypted emails

2014-01-05 Thread Hauke Laging
Am So 05.01.2014, 10:35:44 schrieb Peter Lebbing:

 On 05/01/14 04:38, Hauke Laging wrote:
  You are aware that is doesn't make any sense to make this claim
  without any argument after the opposite has been claimed with an
  argument (a very strong one)?
 
 Eh? You yourself start this whole discussion by making the point that
 it is, as things are now, unreliable to act differently depending on
 whether encryption is applied to the message or not.

There are two different meanings of whether encryption is applied 
which we must tell apart here:

1) The message arrives encrypted.

2) You know that the message has been sent encrypted.


(1) follows from (2) but not the other way round. What I say is:

a) It makes sense to act differently depending on (2).

b) It does not make much sense to act differently depending on (1).

Do you agree on (a) and (b)?

Today you hardly ever have (2). That's what I want to change.


 I really do not understand one bit why you now say this is a claim
 without any argument, I'm quite surprised.

I replied to: One should certainly not act differently depending on the 
encryption of a message.

Maybe there is a misunderstanding (maybe even between the one I replied 
to and the one he replied to). In an earlier mail I have explained (a). 
It seemed to me that he said (a) was wrong without giving any reason for 
that claim. Maybe he meant (b) but that would not have anything to do 
with the discussion I started as (b) is the reason for me starting it.


 I agree with Robert, you're trying to solve a social problem with a
 technical solution.

In my understanding this term refers to problems which are better solved 
socially than technically. But that simply isn't the case here. Why 
should I write I will encrypt this message to 0x12345678 in every mail 
which is boring, easily forgotten and error-prone if the problem can 
*easily* be solved technically with much better results? Why should 
people prefer to have to change their behaviour (social solution) over 
not having to change their behaviour if the second option delivers 
better results with less effort?


There has been an argument of the kind: There is another solution to 
the problem than yours. OK. But that's not the point. The point is: 
Which is better? This is about technical guarantees. How can a social 
approach ever be better than a technical one in that area? GnuPG doesn't 
teach people to create huge keys it prevents it technically. Solving a 
social problem with a technical solution? And if so: Is that a problem?


Hauke
-- 
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Re: sign encrypted emails

2014-01-05 Thread Peter Lebbing
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On 05/01/14 11:15, Hauke Laging wrote:
 Why should I write I will encrypt this message to 0x12345678 in every
 mail which is boring, easily forgotten and error-prone if the problem can
 *easily* be solved technically with much better results?

Don't write I will encrypt this message[1] in every mail hoping that the
recipient deduces that you want to do secret stuff, and leaving them to deduce
from the absence of that message that you want to do the regular stuff. Hoping
that other people will infer meaning from things that are totally not
apparent, /that/ is error-prone.

If someone writes me a signed statement see me tomorrow, I will show up. I
will not come carrying my highly volatile nuclear concoction just because the
message is encrypted. You should feel confident a signed statement is coming
from the person who signed it. You can't deduce very much at all from the
message arriving encrypted, I think. When the message arrives /unencrypted/
and contains confidential stuff, you could show up with a clue-bat and say
Dude, not cool, not cool, because it was obviously (within reason) sent
unencrypted. But it being encrypted means nothing.

The social solution is not include some statement each and every time but
don't deduce anything from it being encrypted. It's not a burden, it's a
change of expectation.

If you want to convey something to someone, just say so. Don't say see me
tomorrow, but say I want to discuss X tomorrow with you, be sure to bring Y.

HTH,

Peter.

[1] By the way, your statement might not even be true; how often have you
written See the attachment and then forgetting to attach the file? I have
done it countless times.

- -- 
I use the GNU Privacy Guard (GnuPG) in combination with Enigmail.
You can send me encrypted mail if you want some privacy.
My key is available at http://digitalbrains.com/2012/openpgp-key-peter

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Re: sign encrypted emails

2014-01-05 Thread Robert J. Hansen
 I agree with Robert, you're trying to solve a social problem with a technical
 solution.

More to the point, he's solving the wrong problem and conflating policy
with mechanism.

GnuPG does not provide policy.  Policy is the responsibility of the
people using GnuPG.  All GnuPG provides is mechanism.

Your problem can be solved trivially by establishing a policy of,
Encrypted messages must contain a notification within the signed
message body of who the message is encrypted for.

For many users this sort of policy is a good idea.  For the majority of
users it's overkill.  Why do you want a policy decision to be
permanently enshrined in GnuPG's mechanism?

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Re: sign encrypted emails

2014-01-05 Thread Robert J. Hansen
 Don't write I will encrypt this message[1] in every mail hoping that the
 recipient deduces that you want to do secret stuff, and leaving them to deduce
 from the absence of that message that you want to do the regular stuff. Hoping
 that other people will infer meaning from things that are totally not
 apparent, /that/ is error-prone.

There also seems to be something else at work here: an allergy to rigor.

GnuPG is most often used in a slipshod, half-thought-through manner.
People don't articulate a security model, much less establish a plan to
mitigate those threats, much less negotiate a policy with their
correspondents to mitigate threats held in common.

Sometime watch the movie _Crimson Tide_.  It's a good action film and
the central premise revolves around a message that violates policy.  A
nuclear ballistic missile submarine is given a legitimate order to
launch missiles at a Russian city.  While preparing to launch, the
submarine receives a second message telling them to abort the launch --
but due to forces beyond their control that message is received only as
a fragment.

The captain refers to the policy: Any message that does not fully
conform to the policy must be completely disregarded.  The captain
insists on launching, since the last policy-conformant message was a
launch order.

The executive officer insists, We received an abort signal; at the very
least we need to delay the launch until we can confirm it.  The
executive officer insists on deviating from policy.

I cannot think of the last time I saw a Hollywood blockbuster that was
built around what is, at its heart, a very technical question about how
high-security communications operate.  It's worth viewing.

The short version is -- if you don't have a policy established, you're
not going to be using GnuPG to provide its fullest amount of
communications security.  That policy also needs to tell people how to
handle messages that don't conform to policy.

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Re: sign encrypted emails

2014-01-05 Thread Hauke Laging
Am So 05.01.2014, 10:15:51 schrieb Robert J. Hansen:

 Your problem can be solved trivially by establishing a policy of,
 Encrypted messages must contain a notification within the signed
 message body of who the message is encrypted for.

That is neither trivial nor reliable nor the best approach to deliver 
this information.


 For many users this sort of policy is a good idea.  For the majority
 of users it's overkill.

Like verifying fingerprints? 8-)


 Why do you want a policy decision to be
 permanently enshrined in GnuPG's mechanism?

As I said in my first mail in this thread this isn't about changing 
GnuPG at all because 

a) this problem is one level above GnuPG

b) GnuPG already has all the capabilities necessary to do this.

As I also said the reason why I have asked this here is the availability 
of people who can make useful comments on that (and are probably 
interested in such general discussions).


Hauke
-- 
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Re: sign encrypted emails

2014-01-05 Thread Robert J. Hansen
 That is neither trivial nor reliable nor the best approach to deliver 
 this information.

It is a trivial fix; whether it is reliable depends on how committed
participants are towards enforcing policy.

 As I said in my first mail in this thread this isn't about changing 
 GnuPG at all because 

Then why are we talking about this?

 As I also said the reason why I have asked this here is the availability 
 of people who can make useful comments on that (and are probably 
 interested in such general discussions).

You are receiving useful comments.  You are choosing to disregard them.  :)




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Re: sign encrypted emails

2014-01-05 Thread Ingo Klöcker
On Sunday 05 January 2014 14:04:49 Peter Lebbing wrote:
 [1] By the way, your statement might not even be true; how often have
 you written See the attachment and then forgetting to attach the
 file? I have done it countless times.

I bet Hauke never forgot to attach the file because he is using KMail 
which warns him about this. Recent Thunderbirds also shows such a 
warning. (I suppose this also counts as technical solution for a social 
problem. ;-) If one always attached the file the second one wrote See 
the attachment, then one'd never forget to attach it and the technical 
solution wouldn't be necessary.)


Regards,
Ingo


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Re: sign encrypted emails

2014-01-05 Thread Leo Gaspard
On Sat, Jan 04, 2014 at 10:28:26PM +0100, Johannes Zarl wrote:
 On Saturday 04 January 2014 16:09:51 Leo Gaspard wrote:
  On Fri, Jan 03, 2014 at 07:31:29PM -0500, Daniel Kahn Gillmor wrote:
   In your example, the fact that a message was encrypted makes the
   recipient treat it as though the sender had indicated something specific
   about the message because it was encrypted.  This is bad policy, since
   there is no indication that the sender encrypted the message themselves,
   or even knew that the message was encrypted.
  
  Which is exactly the reason for which Hauke proposed to sign the encrypted
  message in addition to signing the cleartext message, is it not?
 
 Wouldn't one have to encrypt the signed-encrypted-signed message again to 
 prevent an attacker from stripping away the outer signature? What would the 
 recipient then do with the simple signed-encrypted message?

Well, the idea would be that the receiving program would check there *is* an
additional signature, and refuse it if not.

Nevertheless, adding a second layer of encryption would help, both in avoiding
this threat with less requirements on the receiving program, and in avoiding the
metadata-analysis and irrevocability threat. Less requirements, as the receiving
program merely has to run decrypt-and-check twice, not having to check it
actually has two levels of signature, as any absence of the second level would
be detected by a failed second check. Avoiding metadata analysis, as encrypting
the second signature forbids an attacker to grab a message and have an
undeniable proof that Alice sent an encrypted message to Bob, even without Bob's
help.

  Sure, there might be other ways: add a message stating to which key the
  message is encrypted, etc. But this one has the advantage of requiring
  AFAICT no alteration to the standard, and of being easily automated, for
  humans are quite poor at remembering to always state to which key they
  encrypt.
  
  Anyway, wouldn't you react differently depending on whether a message was
  encrypted to your offline key or unencrypted?
 
 One should certainly not act differently depending on the encryption of a 
 message. Maybe with the one exception of timeliness: If a message is 
 encrypted, you'll probably be ok with me reading the mail when I'm at my home 
 computer. If a message is encrypted to my offline key, you'll be prepared to 
 wait for a month or so (many people have their offline-key in a safe deposit 
 box).
 
 Of course this opens way to subtle timing attacks (delaying reading a message 
 until it is no longer relevant), but these subtle attacks can be done using 
 simpler means (holding the message in transit).

Well... I, personally, would attach more importance (no more validity, just
importance, like in listen to me very well or whatever english people say to
others to get them to listen carefully) to a message signed to an offline main
key that might wait for a month than to a message sent in cleartext. For I would
assume the sender designed his message to be important enough to make me move to
my safe deposit box so as to read it.

Of course, without encryption-checking, this assumption is wrong, and this is
emphasized in one of my previous messages on this thread, with the We got to
talk tomorrow taking importance for the receiver that is unexpected to the
sender, thus leading to a security flaw.

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Re: sign encrypted emails

2014-01-05 Thread Johannes Zarl
On Sunday 05 January 2014 03:10:48 Leo Gaspard wrote:
 Well... I, personally, would attach more importance (no more validity, just
 importance, like in listen to me very well or whatever english people say
 to others to get them to listen carefully) to a message signed to an
 offline main key that might wait for a month than to a message sent in
 cleartext. For I would assume the sender designed his message to be
 important enough to make me move to my safe deposit box so as to read it.

In my feeling this is a rather subjective (to the sender) thing: some people 
encrypt *every* message no matter how trivial. Other people only encrypt those 
messages that match some rather specific criteria. Both kinds of people have 
good reasons for their behaviour. That's the reason why I don't attach an 
intrinsic importance or anything else to the fact that a message is encrypted.

I can see your reasoning behind that message feels more important, and I'm 
quite sure that many people feel that way. It's just that it went away for me 
some time after receiving the n'th encrypted grocery list.

 Of course, without encryption-checking, this assumption is wrong, and this
 is emphasized in one of my previous messages on this thread, with the We
 got to talk tomorrow taking importance for the receiver that is unexpected
 to the sender, thus leading to a security flaw.

Yeah. That's definitely what I meant when I said that one should not act 
differently.

Though if you want a really fancy policy you could require non-encrypted 
messages to be discarded and use the signed-but-not-encrypted communications 
for counter-intelligence. *g* (Yes, I know the flaw here is not-so-subtle...)


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Re: sign encrypted emails

2014-01-05 Thread Doug Barton

-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

On 01/05/2014 08:07 AM, Hauke Laging wrote:
| Am So 05.01.2014, 10:15:51 schrieb Robert J. Hansen:
|
| Your problem can be solved trivially by establishing a policy of,
| Encrypted messages must contain a notification within the signed
| message body of who the message is encrypted for.
|
| That is neither trivial nor reliable nor the best approach to deliver
| this information.

It can be both trivial and reliable, simply place the following in your
.signature file:

I will not encrypt this message before sending.

On those occasions when you do encrypt, remove the word not.

Now your (reasonable) objection is likely to be, But what if the sender
forgets to remove the word 'not'? Well in that case we're right back to
where we started, you cannot solve problems of bad operational practices
with technology. No matter how fool-proof you make the tech, the
universe will come along with a better fool.

Doug

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Re: sign encrypted emails

2014-01-05 Thread Hauke Laging
Am So 05.01.2014, 16:41:11 schrieb Doug Barton:

 It can be both trivial and reliable, simply place the following in
 your .signature file:
 
 I will not encrypt this message before sending.
 
 On those occasions when you do encrypt, remove the word not.

Let me guess: Modifying the mail client so that it automatically removes 
the word not would be illegitimate because for some strange reason 
that would be solving social problems by technical means...
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Re: sign encrypted emails

2014-01-05 Thread Robert J. Hansen
 Let me guess: Modifying the mail client so that it automatically removes 
 the word not would be illegitimate because for some strange reason 
 that would be solving social problems by technical means...

Hauke, at this point you've advocated your idea -- strongly -- and
you've received a general response that is not favorable.  Now, no one
is saying you need to give up on this idea: but if you want to pursue
this idea, you're going to need to implement it yourself.

The best way to prove us wrong is to write a patch that will implement
your idea.  Reality is the ultimate test of all new ideas; make it real,
put it out there, and let the marketplace of ideas choose.

But for now, I don't think you're persuading anyone into implementing
this for you.




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Re: sign encrypted emails

2014-01-05 Thread MFPA
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA512

Hi


On Friday 3 January 2014 at 10:28:28 AM, in
mid:2002014.1ckrbwp...@inno.berlin.laging.de, Hauke Laging wrote:


MFPA:
 Again, this would be flagged up if the sender was in
 the habit of signing outgoing messages (as you
 stated).

 No, it wouldn't. The reason is that the signature is
 created the same  way in the two cases encrypted and
 non-encrypted. Thus you can apply  encryption later
 with the recipient having no chance at all to determine
 who encrypted.

Most signed and encrypted messages created with PGP or GnuPG have
the two processes applied together - you do not normally decrypt a
message and then see a signed message as the output. An exception is
signed and encrypted messages created in the Hushmail web interface.



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Best regards

MFPAmailto:expires2...@ymail.com

Confusion is always the most honest response
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Re: isolating the signature from encrypted data (was: sign encrypted emails)

2014-01-05 Thread Hauke Laging
Am Mo 06.01.2014, 01:47:39 schrieb MFPA:

 Most signed and encrypted messages created with PGP or GnuPG have
 the two processes applied together - you do not normally decrypt a
 message and then see a signed message as the output.

That is correct. I am not aware of a possibility to get the data and the 
signature from GnuPG. But that doesn't mean it's not possible. AFAIK 
there is no difference in the signature in both cases. So it should be 
easy to patch GnuPG in order to get this data (if there isn't another 
OpenPGP implementation which offers this action).

Use both ways (one step, two steps) to sign and encrypt a file and have 
a look at the result with gpg --list-packets.

http://lists.gnupg.org/pipermail/gnupg-users/2004-April/022352.html


Hauke
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Re: sign encrypted emails

2014-01-04 Thread Leo Gaspard
On Fri, Jan 03, 2014 at 07:31:29PM -0500, Daniel Kahn Gillmor wrote:
 On 01/03/2014 06:56 PM, Leo Gaspard wrote:
  On Fri, Jan 03, 2014 at 12:50:47PM -0500, Daniel Kahn Gillmor wrote:
  On 01/03/2014 08:12 AM, Leo Gaspard wrote:
  So changing the encryption could break an opsec.
 
  If someone's opsec is based on the question of whether a message was
  encrypted or not, then they've probably got their cart before their
  horse too.
 
  opsec requirements should indicate whether you encrypt, not the other
  way around.
  
  Well... So, where is the flow in my example? This example was designed so 
  that,
  depending on the level of encryption (and so the importance of the safety 
  of
  the message according to the sender), the message had different meanings.
 
 As you've noticed, the sender cannot verifiably communicate their intent
 by their choice of encryption key.  If the sender wants to communicate
 their intent in a way that the recipient can verify it, they'll need to
 sign something.
 
 In your example, the fact that a message was encrypted makes the
 recipient treat it as though the sender had indicated something specific
 about the message because it was encrypted.  This is bad policy, since
 there is no indication that the sender encrypted the message themselves,
 or even knew that the message was encrypted.

Which is exactly the reason for which Hauke proposed to sign the encrypted
message in addition to signing the cleartext message, is it not?

Sure, there might be other ways: add a message stating to which key the message
is encrypted, etc. But this one has the advantage of requiring AFAICT no
alteration to the standard, and of being easily automated, for humans are quite
poor at remembering to always state to which key they encrypt.

Anyway, wouldn't you react differently depending on whether a message was
encrypted to your offline key or unencrypted?

Cheers,

Leo

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Re: sign encrypted emails

2014-01-04 Thread Johannes Zarl
On Saturday 04 January 2014 16:09:51 Leo Gaspard wrote:
 On Fri, Jan 03, 2014 at 07:31:29PM -0500, Daniel Kahn Gillmor wrote:
  In your example, the fact that a message was encrypted makes the
  recipient treat it as though the sender had indicated something specific
  about the message because it was encrypted.  This is bad policy, since
  there is no indication that the sender encrypted the message themselves,
  or even knew that the message was encrypted.
 
 Which is exactly the reason for which Hauke proposed to sign the encrypted
 message in addition to signing the cleartext message, is it not?

Wouldn't one have to encrypt the signed-encrypted-signed message again to 
prevent an attacker from stripping away the outer signature? What would the 
recipient then do with the simple signed-encrypted message?


 Sure, there might be other ways: add a message stating to which key the
 message is encrypted, etc. But this one has the advantage of requiring
 AFAICT no alteration to the standard, and of being easily automated, for
 humans are quite poor at remembering to always state to which key they
 encrypt.
 
 Anyway, wouldn't you react differently depending on whether a message was
 encrypted to your offline key or unencrypted?

One should certainly not act differently depending on the encryption of a 
message. Maybe with the one exception of timeliness: If a message is 
encrypted, you'll probably be ok with me reading the mail when I'm at my home 
computer. If a message is encrypted to my offline key, you'll be prepared to 
wait for a month or so (many people have their offline-key in a safe deposit 
box).

Of course this opens way to subtle timing attacks (delaying reading a message 
until it is no longer relevant), but these subtle attacks can be done using 
simpler means (holding the message in transit).

Cheers,
  Johannes

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Re: sign encrypted emails

2014-01-04 Thread Hauke Laging
Am Sa 04.01.2014, 22:28:26 schrieb Johannes Zarl:

 Wouldn't one have to encrypt the signed-encrypted-signed message again
 to prevent an attacker from stripping away the outer signature? What
 would the recipient then do with the simple signed-encrypted message?

That would be possible for an attacker but not make any sense: If the 
recipient expects the outer signature (only then this feature is a 
protection like signing is a protection only if the recipient acts 
differently on signed vs. non-signed messages) then the attacker is 
discovered without any advantage.

There is another reason for creating this fourth layer: Some people want 
to hide the metadata (who made the signature).


 One should certainly not act differently depending on the encryption
 of a message.

You are aware that is doesn't make any sense to make this claim without 
any argument after the opposite has been claimed with an argument (a 
very strong one)?


Hauke
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Re: sign encrypted emails

2014-01-03 Thread Hauke Laging
Am Fr 03.01.2014, 00:33:51 schrieb Doug Barton:
 On 01/02/2014 09:35 PM, Hauke Laging wrote:
 | I just noticed that you can easily be deluded about an email being
 | encrypted: That you receive an encrypted mail does not mean that it
 | was sent encrypted. An adversary may encrypt a non-encrypted message
 | (which he has intercepted) in order to create more trust in the
 | message for the recipient: If you receive critical information and
 | are aware that it has not been encrypted then you may react
 | differently from the case where you are sure that is was encrypted.
 
 This threat model doesn't make a lot of sense, except for very naive
 users who cannot distinguish the importance of a message that is
 encrypted vs. a message (encrypted or not) which is signed.

I am quite sure you have misunderstood something. Sorry if I didn't make 
myself clear.

Do you agree that it is (or, depending on the content, can be) an important 
information whether a message was encrypted by the sender (and for which key)? 
How can it make little sense to provide this information?

Whether it is more important to encrypt a message or to sign it differs a lot 
with the content. Thus I do not understand your explanation of importance.

This is similar to SSL/TLS without client negotiation: The client knows (or: 
can know) whether it is encrypting for the right server. But the server cannot 
know whether the legitimate client has started the connection or an MitM 
attacker. If the server demands certainty about that then it has to require 
the use of client certificates.

But currently there is (AFAIK) no such thing as an analog for the client 
certificate in the OpenPGP world. The certificate itself is already there, of 
course, but it is not yet used in a way providing security for the recipient 
about the confidentiality of the message.


Hauke
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Re: sign encrypted emails

2014-01-03 Thread Doug Barton

-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

FYI, your client has horrible line wrapping. If there is a setting,
please change it to 72 columns.

On 01/03/2014 12:59 AM, Hauke Laging wrote:

| Do you agree that it is (or, depending on the content, can be) an
| important information whether a message was encrypted by the sender
| (and for which key)?

Not particularly, no. The message doesn't get encrypted using the
sender's key, although it may be encrypted to the sender's key, along
with the recipient's.

What advantage does it give to the attacker to encrypt a message via
MITM? The likely outcome of doing so would be to reveal that they are
intercepting messages, for what benefit? That's a legitimate question,
not a snark. You seem to be suggesting that this would provide value to
the attacker, if so can you elaborate?

| How can it make little sense to provide this information?

If the sender cares they can insert a statement in their signed message.
I did/did not encrypt this message before sending. Problem solved.

| Whether it is more important to encrypt a message or to sign it
| differs a lot with the content. Thus I do not understand your
| explanation of importance.

My argument is that the _only_ thing relevant to message validity is the
signature on the message itself. Whether it was encrypted or not should
play no role in the recipient's calculation of the validity of the message.

| This is similar to SSL/TLS without client negotiation:

No, it's not at all. But I don't want to quibble about that, I'm still
interested in your description of the importance of the encryption
itself, separate from the message and signature.

Doug
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Re: sign encrypted emails

2014-01-03 Thread Doug Barton

-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

On 01/03/2014 01:13 AM, Doug Barton wrote:
| My argument is that the_only_  thing relevant to message validity
| is the signature on the message itself. Whether it was encrypted or
| not should play no role in the recipient's calculation of the
| validity of the message.

Sorry, that's a little bit stronger than I intended.  There are of
course cases such as, This is odd, every communication I have ever
had with Alice about $SUBJECT previously has been encrypted, but this
one is not, I wonder if there is a problem here? But for the common
case my point remains  the fact that a message is encrypted should
not enter into the validity calculation.

Doug

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Version: GnuPG v2.0.20 (GNU/Linux)

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Re: sign encrypted emails

2014-01-03 Thread Robert J. Hansen
On 1/3/2014 3:33 AM, Doug Barton wrote:
 This threat model doesn't make a lot of sense, except for very naive
 users who cannot distinguish the importance of a message that is
 encrypted vs. a message (encrypted or not) which is signed.

I'm going to cautiously disagree.  What we call very naive users
account for the vast majority of GnuPG users.

Unfortunately, that's as far as my disagreement goes.  I see what
Hauke's getting at, but I disagree that it really amounts to much of a
problem, or that his proposed fix would work.

The real problem Hauke's discovered is, people generally don't have the
educational background to think formally and critically about trust.
Which is, well, true -- but that one's a hell of a hard problem to
solve.  Everything else (including sign-encrypt-sign schemes) amounts
to just ways to try to dodge the real issue.

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Re: sign encrypted emails

2014-01-03 Thread Hauke Laging
Am Fr 03.01.2014, 01:13:13 schrieb Doug Barton:

 On 01/03/2014 12:59 AM, Hauke Laging wrote:
 | Do you agree that it is (or, depending on the content, can be) an
 | important information whether a message was encrypted by the sender
 | (and for which key)?
 
 Not particularly, no. The message doesn't get encrypted using the
 sender's key, although it may be encrypted to the sender's key, along
 with the recipient's.

That's not what I am talking about. I am talking about the recipient 
having keys with different security levels. So there are keys I 
(insecure) and S (secure). By insecure I mean a key like the one which 
signs this email: Being used on a normal system (i.e. an insecure one; 
oh no, in a moment Rob will notice that I used secure and insecure 
again...).

If data is so important that it shall not be encrypted for my key I but 
for my key S only then I want to be sure that it has been encrypted by 
the sender for S. That the message which arrives at me is encrypted for 
S does not ensure this. Anyone can encrypt messages for my key.


 What advantage does it give to the attacker to encrypt a message via
 MITM?

As I said: If a normal user (i.e. one with nearly no security clue at 
all) starts an email conversation without encryption (or with weak 
encryption) and I notice that (because the message arrives unchanged) 
then I will tell the sender to change his behaviour. He will probably to 
that and the communication becomes secure.

It is in the interest of an adversary to prevent the communication from 
becoming secure.


 The likely outcome of doing so would be to reveal that they are
 intercepting messages,

In my opinion it is very unlikely that this would be revealed. There are 
people who like to get everything encrypted and those who prefer to get 
only important data encrypted. Every serious adversary will know what 
type his target is. This is more or less a public information.

So if somebody wants everything encrypted why should he ever ask or 
mention that? It is possible, yes. Thanks for encrypting your 
messages. Who does that? And how many senders unfamiliar with crypto 
would understand from that that their message has been modified? Maybe a 
nice feature of their great ISP? Even worse with asking such a sender 
whether he has used the right recipient key. Probably he will not even 
understand the problem or misassess the situation.

And if the recipient expects only important data to be encrypted then 
the adversary would encrypt only important data (which may be hard to 
decide automatically though but who would notice a minute delay under 
normal circumstances?).

And why should the adversary not risk being detected? We encrypt because 
we assume that there are adversaries.


 | How can it make little sense to provide this information?
 
 If the sender cares they can insert a statement in their signed
 message. I did/did not encrypt this message before sending. Problem
 solved.

Yes. But why should the sender care? The sender can be sure about doing 
it right! The recipient is the one who cannot. And why should we bother 
writing that in every mail if there is a simple automatic solution to 
it? You cannot even be sure that the information is correct! People make 
mistakes.


 My argument is that the _only_ thing relevant to message validity is
 the signature on the message itself.

I do not doubt that in any way but my argument isn't about validity at 
all. It is about guaranteed confidentiality! That is a big difference.


Hauke
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Re: sign encrypted emails

2014-01-03 Thread Hauke Laging
Am Fr 03.01.2014, 10:02:28 schrieb MFPA:

 OpenPGP's mitigation against this is signing emails, and the web of
 trust to give assurance who signed.

That's exactly why I want signatures. But I do not only want a signature 
which guarantees the data integrity, I want a(nother) signature which 
guarantees the (correct) encryption.


 You mean the recipient has 2 keys, one of which the adversary has
 compromised? And the adversary intercepts and decrypts mail that is
 encrypted to the compromised key, then sends it on its way encrypted
 to the non-compromised key?

Yes, that is the more complicated case.


 Again, this would be flagged up if the
 sender was in the habit of signing outgoing messages (as you stated).

No, it wouldn't. The reason is that the signature is created the same 
way in the two cases encrypted and non-encrypted. Thus you can apply 
encryption later with the recipient having no chance at all to determine 
who encrypted.


  (this may mean that you sign it twice: once
  before and once after encryption).
 
 Is that better than the usual signing and encryption carried out
 together?

It is better with respect to ensuring the encryption. It has 
disadvantages, though, otherwise we wouldn't do it the other way round. 
Proving the authenticity becomes more difficult if there is no signature 
within the encryption because a third party cannot encrypt the data. You 
would need to give them the session key. Who is capable of doing that? 
Furthermore you cannot know whether an encrypted message has been signed 
within. That may be an advantage in certain situations. You can send an 
encrypted message anonymously. That is not possible with my proposal 
(you would have to add a fourth layer... not difficult though).

But I do not suggest to make my configuration the default. I just want 
to be able to use it. Sometimes it's best to send a signed cleartext 
message, sometimes to send an unsingned encrypted message, sometimes a 
first signed then encrypted message and I want to stress that sometimes 
it's best to send a first encrypted then signed (or signed-encrypted-
signed) message.


 Both your examples seem to involve encrypted-only and not signed
 messages,

The problem is the same with signed and unsigned messages.


 so would be unaffected by introducing additional signature
 options.

I don't understand that statement.


Hauke
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Re: sign encrypted emails

2014-01-03 Thread Hauke Laging
Am Fr 03.01.2014, 04:28:38 schrieb Robert J. Hansen:

 or that his proposed fix would work.

Would you explain how that shall be avoided?

You send an email to me. You encrypt it to the key which I want you to 
encrypt it to. Then you sign the encrypted data.

If I receive an email from you which is not encrypted and signed (as the 
outer layer) then I go on red alert. Like today I might if the message 
is not encrypted or not signed.

How shall THEY create an encrypted-signed message if you have e.g. sent 
it without encryption? The adversary needs your signing key.


Hauke
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Re: sign encrypted emails

2014-01-03 Thread Robert J. Hansen
On 1/3/2014 4:57 AM, Hauke Laging wrote:
 Would you explain how that shall be avoided?

I already did, in quite clear language.

You are trying to solve a social problem (people don't have the
background to think formally about trust issues) via technological
means (if we just change the way we sign...).


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Re: sign encrypted emails

2014-01-03 Thread Peter Lebbing
On 03/01/14 10:57, Hauke Laging wrote:
 If I receive an email from you which is not encrypted and signed (as the 
 outer layer) then I go on red alert. Like today I might if the message is
 not encrypted or not signed.

How do you know the sender doesn't have an unencrypted copy of the message in
an easily broken into online backup service? The encryption of one copy of a
message doesn't imply the confidentiality of all copies that exist.

HTH,

Peter.

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You can send me encrypted mail if you want some privacy.
My key is available at http://digitalbrains.com/2012/openpgp-key-peter

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Re: sign encrypted emails

2014-01-03 Thread Leo Gaspard
On Fri, Jan 03, 2014 at 06:21:05AM -0500, Robert J. Hansen wrote:
 On 1/3/2014 4:57 AM, Hauke Laging wrote:
  Would you explain how that shall be avoided?
 
 I already did, in quite clear language.
 
 You are trying to solve a social problem (people don't have the
 background to think formally about trust issues) via technological
 means (if we just change the way we sign...).

I think the need for such a fix could also be highlighted in the following
example.

I sign the message Got to talk tomorrow at dawn, then send it to Alice,
thinking about the cake for the birthday party, not important so not encrypting
it. Bob grabs the message, and sends it encrypted to Alice's highest security
key. Alice then thinks it is a really important message, and the matters to
discuss are really important. She takes with her the top secret files we are
working together on.  Bob, knowing the place and date of the meeting, then comes
and steals the top secret files.

So changing the encryption could break an opsec.

I'm not saying it would be useful everyday. But some use cases seem to require
it. However, I'm not saying this feature should be included by default, as a fix
would be easy (call gpg twice), and I can think of few use cases.

BTW, is a timestamp included in the signature? If not, it could lead to similar
issues.

Cheers,

Leo

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Re: sign encrypted emails

2014-01-03 Thread Daniel Kahn Gillmor
On 01/03/2014 08:12 AM, Leo Gaspard wrote:
 So changing the encryption could break an opsec.

If someone's opsec is based on the question of whether a message was
encrypted or not, then they've probably got their cart before their
horse too.

opsec requirements should indicate whether you encrypt, not the other
way around.

 BTW, is a timestamp included in the signature? If not, it could lead to 
 similar
 issues.

Yes, all OpenPGP signatures generated by standards-compliant tools
include a timestamp:

 https://tools.ietf.org/html/rfc4880#section-5.2.3.4

--dkg



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Re: sign encrypted emails

2014-01-03 Thread Daniel Kahn Gillmor
On 01/03/2014 12:35 AM, Hauke Laging wrote:
 From the RfC perspective (PGP/MIME) this should not be a problem; you just 
 need another level of nesting. Maybe the mail clients are not even prepared 
 for reading such messages. That would not surprise me but would not be an 
 argument against one client implementing this as the first one. I am 
 interested in general arguments for and against this.

it sounds to me like you might be interested in what the S/MIME
community calls triple-wrapping, which is used to provide
cryptographic proof-of-origin and attribute-handling for intermediate
transport agents:

 http://www.isode.com/whitepapers/smime-military-messaging.html
 https://bugzilla.mozilla.org/show_bug.cgi?id=380624

That said, triple-wrapping (or similar approaches) have tradeoffs that
we might not want to encourage.

For example, they leak metadata about who signed the message to anyone
who observes it in transit; this is not the case for the traditional
sign-then-encrypt layering.  metadata gathering is a fruitful
surveillance technique.

but at its core, i think the problem you're raising is related to a
fundamental (but probably common) misunderstanding: people assume that
if something is encrypted to them then that is related to some signal
from the message author, even though asymmetric encryption has nothing
to do with authenticity or verifiability.

I don't think you're going to solve that particular problem by having
some e-mails have an extra layer of signature on them.

--dkg



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Re: sign encrypted emails

2014-01-03 Thread NdK
Il 03/01/2014 11:28, Hauke Laging ha scritto:

 But I do not suggest to make my configuration the default. I just want 
 to be able to use it. Sometimes it's best to send a signed cleartext 
 message, sometimes to send an unsingned encrypted message, sometimes a 
 first signed then encrypted message and I want to stress that sometimes 
 it's best to send a first encrypted then signed (or signed-encrypted-
 signed) message.
I can't come up with a situation where sign, encrypt, sign again w/
*same* key used in the first signature gives more security than first
encrypt then sign. So two layers are enough.

I (partially) get your point: receiving an encrypted message could
mislead an uneducated user... But I doubt someone w/ access to top
secret material falls in that category :)

BYtE,
 Diego.

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Re: sign encrypted emails

2014-01-03 Thread Leo Gaspard
On Fri, Jan 03, 2014 at 12:50:47PM -0500, Daniel Kahn Gillmor wrote:
 On 01/03/2014 08:12 AM, Leo Gaspard wrote:
  So changing the encryption could break an opsec.

 If someone's opsec is based on the question of whether a message was
 encrypted or not, then they've probably got their cart before their
 horse too.

 opsec requirements should indicate whether you encrypt, not the other
 way around.

Well... So, where is the flow in my example? This example was designed so that,
depending on the level of encryption (and so the importance of the safety of
the message according to the sender), the message had different meanings.

Sorry, I can't see yet where I went wrong.

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Re: sign encrypted emails

2014-01-03 Thread Daniel Kahn Gillmor
On 01/03/2014 06:56 PM, Leo Gaspard wrote:
 On Fri, Jan 03, 2014 at 12:50:47PM -0500, Daniel Kahn Gillmor wrote:
 On 01/03/2014 08:12 AM, Leo Gaspard wrote:
 So changing the encryption could break an opsec.

 If someone's opsec is based on the question of whether a message was
 encrypted or not, then they've probably got their cart before their
 horse too.

 opsec requirements should indicate whether you encrypt, not the other
 way around.
 
 Well... So, where is the flow in my example? This example was designed so 
 that,
 depending on the level of encryption (and so the importance of the safety of
 the message according to the sender), the message had different meanings.

As you've noticed, the sender cannot verifiably communicate their intent
by their choice of encryption key.  If the sender wants to communicate
their intent in a way that the recipient can verify it, they'll need to
sign something.

In your example, the fact that a message was encrypted makes the
recipient treat it as though the sender had indicated something specific
about the message because it was encrypted.  This is bad policy, since
there is no indication that the sender encrypted the message themselves,
or even knew that the message was encrypted.

--dkg




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Re: sign encrypted emails

2014-01-03 Thread Doug Barton

On 01/03/2014 01:28 AM, Robert J. Hansen wrote:

On 1/3/2014 3:33 AM, Doug Barton wrote:

This threat model doesn't make a lot of sense, except for very naive
users who cannot distinguish the importance of a message that is
encrypted vs. a message (encrypted or not) which is signed.


I'm going to cautiously disagree.  What we call very naive users
account for the vast majority of GnuPG users.


I don't necessarily disagree with you on that. :)


Unfortunately, that's as far as my disagreement goes.  I see what
Hauke's getting at, but I disagree that it really amounts to much of a
problem, or that his proposed fix would work.

The real problem Hauke's discovered is, people generally don't have the
educational background to think formally and critically about trust.
Which is, well, true -- but that one's a hell of a hard problem to
solve.  Everything else (including sign-encrypt-sign schemes) amounts
to just ways to try to dodge the real issue.


Yes, that is the point I was trying to get across.

... and I did actually suggest a solution to the problem Hauke is 
(ostensibly) trying to solve. The sender can include a statement in 
their signed message regarding whether or not they also encrypted it 
before sending. However I would still argue that doing so would have no 
real benefit.


Thinking further, what *may* be useful would be for the mail client to 
pop up a message that says something similar to, This message was 
encrypted, but not signed. No assumptions should be made about the 
validity of the message itself.


In the end however there is no substitute for user education. :-/

Doug


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sign encrypted emails

2014-01-02 Thread Hauke Laging
Hello,

this is not a GnuPG problem. GnuPG is capable of doing what I want. But I am 
interested in your opinion.

I just noticed that you can easily be deluded about an email being encrypted: 
That you receive an encrypted mail does not mean that it was sent encrypted. 
An adversary may encrypt a non-encrypted message (which he has intercepted) in 
order to create more trust in the message for the recipient: If you receive 
critical information and are aware that it has not been encrypted then you may 
react differently from the case where you are sure that is was encrypted.

Or similar: A message is encrypted to a low security key which has been 
compromised (unnoticed by the recipient). The adversary decrypts the message 
ans reencrypts it to a more secure key.

This can be detected by asking the sender (which noone would do every time) or 
by signing the encrypted message (this may mean that you sign it twice: once 
before and once after encryption).

I would like to ask mail client developers to add this feature. But before I 
would like to hear opinions whether that makes sense.

From the RfC perspective (PGP/MIME) this should not be a problem; you just 
need another level of nesting. Maybe the mail clients are not even prepared 
for reading such messages. That would not surprise me but would not be an 
argument against one client implementing this as the first one. I am 
interested in general arguments for and against this.

I have tried to create a test file. Unfortunately I am not sure whether I have 
done that correctly. I am familiar with checking MIME signatures with gpg 
directly but creating a message is a different story:

http://www.crypto-fuer-alle.de/docs/sign-encrypt-sign/demo.mbox

KMail ignores the outer signature layer in its main window but shows the 
structure correctly in the lower part of the window. That could mean that my 
file is correct but KMail not prepared to display it correctly.

Enigmail tells me that might be a signed message but doesn't show anything.

If I encrypt some text manually and paste it as body content in a PGP/MIME 
mail which gets signed and encrypted then KMail shows all three layers in its 
main window. This could indicate that KMail is capable of handling three 
layers but that my test file is incorrect.


Hauke
-- 
Crypto für alle: http://www.openpgp-schulungen.de/fuer/unterstuetzer/
http://userbase.kde.org/Concepts/OpenPGP_Help_Spread
OpenPGP: 7D82 FB9F D25A 2CE4 5241 6C37 BF4B 8EEF 1A57 1DF5


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