Re: [Enigmail] test implementation for auto encryption available in test-branch

2014-04-20 Thread Patrick Brunschwig
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On 20.04.14 15:30, Nicolai Josuttis wrote:
 Hi all,
 
 as announced some weeks ago, I just pushed a patch for a first
 implementation to provide the ability to automatically encrypt
 messages if all valid keys are known without the need to have a
 rule for it into the sub-branch (derived from master): 
 AutoSendEncrypted
 
 In fact, you can choose between:
 Automatically send encrypted? - Never No automatically encrypted
 sending except explicitly triggered by rules - With full trust 
 Automatically send encrypted when all keys are known and valid
 and have full trust - With marginal trust Automatically send
 encrypted when all keys are known and valid and have at least
 marginal trust - With unknown trust Automatically send encrypted
 when all keys are known and valid and have no explicit mistrust
 
 With this patch I also change the ability to ask for confirmations 
 before sending with more options:
 Confirm before sending? - Never Don't display information dialog
 about signing/encryption before sending a message - Always Always
 display information dialog about signing/encryption before
 sending a message - If encrypted Display information dialog about
 signing/encryption before sending an ENCRYPTED message - If
 unencrypted Display information dialog about signing/encryption
 before sending an UNENCRYPTED message - If rules changed
 encryption Display information dialog about signing/encryption
 before sending if encryption was changed by a rule or
 auto-encryption
 
 Because this is a non-trivial patch, I want to give the opportunity
 to validate it before it is merged into the master. You have to
 switch to the sub branch: git checkout AutoSendEncrypted and build
 and install the xpi: configure make make xpi
 
 NOTE: At least one thing is MISSING: - the migration from the old
 preference confirmBeforeSend (bool) to the new confirmBeforeSending
 (int) QUESTION: To test the migration I need a new version number
 in the code The code still has 1.6. Is 1.7 appropriate? Where the
 THE right place to change that?

The only place this is relevant is in install.rdf. Release numbers are
not only technically driven. Therefore I only modify this once I
decide to create a new release.

 Please give any feedback you have. The goal is to push it ASAP into
 the master (as both features are something I'd really like to
 have).

Even though setting up a build environment is easier than in the past,
I still don't think that everyone will want to do so. I have created a
package to download for Windows, Linux and Mac OS X:

https://www.enigmail.net/download/beta/enigmail-1.7a1pre-test.xpi

- -Patrick
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Re: [Enigmail] test implementation for auto encryption available in test-branch

2014-04-20 Thread Nicolai Josuttis
 On 20.04.14 15:30, Nicolai Josuttis wrote:
 as announced some weeks ago, I just pushed a patch for a first 
 implementation to provide the ability to automatically encrypt 
 messages if all valid keys are known without the need to have a 
 rule for it into the sub-branch (derived from master): 
 AutoSendEncrypted
...

Am 20.04.2014 16:48, Patrick Brunschwig schrieb/wrote:
 Even though setting up a build environment is easier than in the
 past, I still don't think that everyone will want to do so. I have
 created a package to download for Windows, Linux and Mac OS X:
 
 https://www.enigmail.net/download/beta/enigmail-1.7a1pre-test.xpi

Thanks a lot, Patrick.

For those testing it I have a specific question:
The new model provides different options to auto send encrypted
based on the owner trust of the keys.

Options are roughly:
- never auto encrypt (except by rules)
- always auto encrypt if all keys known (except keys with mistrust)
- auto encrypt if all keys known and having full owner trust
- auto encrypt if all keys known and having at least marginal trust
(yes, the current labels can be improved)

Question:
- Is this too fine grained?
- Or is this even confusing
  (because now if I select the second option,
   it ignores always trust all keys being off).
Another simpler model would be:
- never
- if all keys are known
- if all keys are known and trusted
  (but here we must define what trusted means)

Also I wonder whether the options should be in the sending
or key selection tab.
I preferred sending because in principle this option
has the power to allow especially newbies to
ignore recipient rules by still encrypting if useful
and possible.
- Either having the keys is enough
- Or having the keys and explicitly having raised trust
  is enough.
  But then the difference between full and marginal might be helpful.

Nico


-- 
Nicolai M. Josuttis
www.josuttis.de

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Re: [Enigmail] test implementation for auto encryption available in test-branch

2014-04-20 Thread Nicolai Josuttis
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Am 20.04.2014 21:38, Philip Jackson schrieb/wrote:
 Hi Nicolai,
 
 I've downloaded and installed the 1.7a1pre-test version.
 Patrick's link shouldn't just be clicked on though.  Firefox
 downloaded it and tried to install and then rejected it as 'not
 being suitable for Firefox' and then presumably deleted it (because
 I couldn't find it in the downloads directory).
 
 However, one question :  in the preferences/sending tab, how do 
 your new options cohabit with the second check box item 'Always 
 trust people's valid keys' ?
 

 Does that option cancel your 3 options for full, marginal, unknown 
 trust levels?
 
No, it's the other way round:
Currently the options don't affect each other (which might be wrong).

That is:
- - I can select to auto send encrypted emails
  to people for which the keys have unknown trust
  although always trust is NOT selected.
- - I was thinking about some alternatives, though.
  One is that if not always trust all keys is selected
  I disable the last (two) options.
  That would be a visual feedback for what you asked.
- - Another is that the auto-send-options only ask whether to send
  encrypted if all keys are known and trusted
  and what trusted means is derived from the
  always trust all keys option.

In any case I am not sure whether the whole approach
I programmed is good/intuitive.
So allow me to explain some details of the current implementation:

- - Option always trust all keys is enabling or disabling the option
  --trust-model always
  This is documented in the GPG manual as:
   Skip key validation and assume that used keys are always fully
trusted.
   You generally won't use this unless you are using some external
validation scheme.
   This option also suppresses the [uncertain] tag printed with
signature checks when there is no evidence that the user ID is bound
to the key.
  Sounds pretty dangerous (but is often selected).

- - My options affect whether and how the Key Validity and Owner Trust
  columns of the key management are considered.
  For example, if I need marginal trust,
  both columns have at least to have that level.
  (Note that validity/trust is sorted according to:
- disabled/revoked/expired
- explicit mistrust
- unknown trust
- marginal trust
- full/ultimate trust
   )
  auto send encrypted would never happen with keys being in the
  first two groups. No option should change that IMO.
  For the other three groups,
  I have provided the three auto-send-enc-options.

However, now we have different trust models
(one by GPG and one by the key manager)
THis also can be confusing.
On the other hand,
dealing with what is defined in the key management dialog
can be more intuitive than dealing with the rules of
the web of trust.

Consider for a moment we would have no recipient rules
and people don't know the rules of the web of trust.
The simple approach for the novice either would be:
 a) You can disable auto encrypt.
Then you have your general default about whether to encrypt
which you can change for each mail.
 b) You can select to auto encrypt if all keys are known
(ignoring the trust level, but not mistrust or revoke/expired).
This is like selecting always trust all keys
(and as dangerous)
 c) You can select to auto encrypt only if keys are known
AND you have declared some trust.
In my implementation you can either require
at least either marginal or full trust.

The current approach I implemented gives you this principle,
with the behavior that for b) and c) always trust all keys
doesn't matter.
If I give always trust all keys a semantics here,
the effect would be to let c) and b) behave the same
if always trust all keys is enabled.
May be that's more intuitive.
Especially if I disable the last two options
when always trust all keys is selected.

But is all might be too complicated ...
(for novices or experts or both?).
Hmmm, questions over questions ...
As I wrote: I am not sure.
Opinions please.

 Nico


 - Philip Jackson 
 Tel : (+33) 468 49 80 53GnuPG Public Key : 0x23543A63.asc
 
 On 20/04/2014 19:35, Nicolai Josuttis wrote:
 The new model provides different options to auto send encrypted 
 based on the owner trust of the keys.
 
 Options are roughly: - never auto encrypt (except by rules) - 
 always auto encrypt if all keys known (except keys with
 mistrust) - auto encrypt if all keys known and having full owner
 trust - auto encrypt if all keys known and having at least
 marginal trust (yes, the current labels can be improved)
 
 
 
 ___ enigmail-users 
 mailing list enigmail-users@enigmail.net 
 https://admin.hostpoint.ch/mailman/listinfo/enigmail-users_enigmail.net


 
- -- 
Nicolai M. Josuttis
www.josuttis.de

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Re: [Enigmail] test implementation for auto encryption available in test-branch

2014-04-20 Thread Philip Jackson
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On 21/04/2014 00:12, Nicolai Josuttis wrote:
 
 
 Am 20.04.2014 21:38, Philip Jackson schrieb/wrote:
 Hi Nicolai,
 
 I've downloaded and installed the 1.7a1pre-test version. Patrick's link
 shouldn't just be clicked on though.  Firefox downloaded it and tried to
 install and then rejected it as 'not being suitable for Firefox' and then
 presumably deleted it (because I couldn't find it in the downloads
 directory).
 
 However, one question :  in the preferences/sending tab, how do your new
 options cohabit with the second check box item 'Always trust people's
 valid keys' ?
 
 
 Does that option cancel your 3 options for full, marginal, unknown trust
 levels?
 
 No, it's the other way round: Currently the options don't affect each other
 (which might be wrong).
 
 That is: - I can select to auto send encrypted emails to people for which
 the keys have unknown trust although always trust is NOT selected. - I
 was thinking about some alternatives, though. One is that if not always
 trust all keys is selected I disable the last (two) options. That would be
 a visual feedback for what you asked. - Another is that the
 auto-send-options only ask whether to send encrypted if all keys are known
 and trusted and what trusted means is derived from the always trust
 all keys option.

In any case, I think the display of your new options at the same time
as the second check box item (Always trust people's valid keys)
presents a confusing display.  A display logic should be decided
that prevents them both being displayed at the same time.

 In any case I am not sure whether the whole approach I programmed is
 good/intuitive. So allow me to explain some details of the current
 implementation:
 
 - Option always trust all keys is enabling or disabling the option 
 --trust-model always This is documented in the GPG manual as:
 Skip key validation and assume that used keys are always fully
 trusted.
 You generally won't use this unless you are using some external
 validation scheme.
 This option also suppresses the [uncertain] tag printed with
 signature checks when there is no evidence that the user ID is bound to the
 key. Sounds pretty dangerous (but is often selected).

see below -

 
 - My options affect whether and how the Key Validity and Owner Trust 
 columns of the key management are considered. For example, if I need
 marginal trust, both columns have at least to have that level. (Note that
 validity/trust is sorted according to: - disabled/revoked/expired -
 explicit mistrust - unknown trust - marginal trust - full/ultimate trust ) 
 auto send encrypted would never happen with keys being in the first two
 groups. No option should change that IMO. For the other three groups, I
 have provided the three auto-send-enc-options.
 
 However, now we have different trust models (one by GPG and one by the key
 manager) THis also can be confusing. On the other hand, dealing with what
 is defined in the key management dialog can be more intuitive than dealing
 with the rules of the web of trust.
 
 Consider for a moment we would have no recipient rules and people don't
 know the rules of the web of trust. The simple approach for the novice
 either would be: a) You can disable auto encrypt. Then you have your
 general default about whether to encrypt which you can change for each
 mail. b) You can select to auto encrypt if all keys are known (ignoring the
 trust level, but not mistrust or revoke/expired). This is like selecting
 always trust all keys (and as dangerous)

The question of 'dangerous' puzzles me somewhat.  Where is the danger in
trusting a key ?   You are implying that one should not encrypt to a person
whose key is untrusted - whether in the sense of its validity or of its
owner's trust.

There could be danger to some people in the mere act of being seen, by an
observer, to be using encryption and in those circumstances, the
trustworthiness of the owner or the key would be irrelevant.

But even if the key validity has been fully ascertained, and the owner is
'fully trusted' in the sense that applies to the web of trust, one would have
to consider the nature of the material (secrets) being written in the message
- - and here again, the gpg trustworthiness of the owner and the key validity
are not the most relevant factors.   What is more relevant are the personal
qualities of the owner - will he betray you ?, is he a stooge planted by the
enemy/competitor?  These are not questions that gpg web of trust or key
validity can answer.

My thoughts are that the more emails that can be encrypted, the better.  A
higher volume of encrypted mails provides a better safety screen for all so it
is better to 'trust all keys' and to be extremely careful what you write if
you do not know the recipient.

 c) You can select to auto encrypt only if keys are known AND you have
 declared some trust. In my implementation you can either require at least
 either marginal or full trust.
 
 

Re: [Enigmail] test implementation for auto encryption available in test-branch

2014-04-20 Thread Daniel Kahn Gillmor
On 04/20/2014 07:12 PM, Daniel Kahn Gillmor wrote:

 I think it's a really bad idea to make encryption contingent on trust
 settings; it should only be contingent on validity.

let me explain this a bit further:

 * setting non-zero ownertrust on someone's keys puts you at risk of
being willing to believe any faulty certifications that they make.

 * therefore, you should only set ownertrust on a key if you think that
the keyholder makes reasonable certifications.

 * any tool which changes its behavior in ways unrelated to reliability
of a keyholder's certifications on the basis of how much ownertrust
you've set on the key will encourage some people to set ownertrust for
these other effects.

 * the result will be that those users will end up willing to rely on
certifications that they really do not want to rely on.

does this make sense?  any auto-encrypt mode needs to be based strictly
on certificate validity (for the e-mail addresses being sent to, not for
any other User ID on the key), and *not* on key ownertrust.

--dkg



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