Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Andrew Feinberg
Let's first have context -- at this time I am a 30 year old journalist. But (to 
establish my geek bona fides) shortly after I could legally drive, but long 
before I could vote, I went through the process of becoming a registered Debian 
Linux developer.  

Then, as is the case now, to achieve that status, one needs to have their GnuPG 
key (back then PGP) signed by a fellow developer who has verified their 
identity. 

While I had undergone the process with my PGP key back when I was a high school 
student, by the time Debian made the switch to GPG (as I recall for ideological 
reasons surrounding PGP's license) I was at university with far less free time, 
and learning crypto software or getting your keys exchanged and signed wasn't 
easy. And so I never made the time to learn the new software until recent 
events led me to revisit my options.

I haven't been a regular Linux user since 2001 (switched to Apple) but I've 
tried available tools for Linux and what's out there for Mac OS, even trying to 
compile some F/OSS solutions from scratch on Mac OS. And to be honest, despite 
all the innovations in user interface over the past 12 years, the situation 
doesn't look to have changed much since 2001.

Now, I realize that for someone whose very life might depend on strong 
encryption that works, their incentive to learn even the most arcane and 
user-unfriendly software could be high enough to overcome any resistance due to 
either inertia, poor design, or any other conceivable reason why Joe Public 
wouldn't make everyday use of the stuff.

These days I'm a journalist, and while my work has rarely taken me into places 
or subjects where encryption is needed, recent events have inspired me to 
venture back into the available tools to see if I could make using email with 
strong cryptography easy enough that I could suggest it to regular sources for 
everyday use.

It still sucks. What exists is godawful at worse and cumbersome at best. 

For a cryptosystem to really, and I mean really become widespread enough to 
make an impact, it needs to be designed and implemented in such a way that a 
given user who wants to add that level of security to his** email need only 
install at the very least some manner of plugin to an existing client, or at 
most switch to an easy to use replacement which has that functionality built in 
seamlessly. Key exchange would have to be as easy as forming connections on a 
social network. Heck, a crypto-social network might be the best way to 
jump-start such a thing.

But let's be honest here -- I think we all are aware on some level or another 
that even if one was able to develop and deploy the easiest software imaginable 
(say, Apple's iCrypt that they'd allowed to be vetted, even made key parts 
open source)  and the most robust algorithms known to man, it's not enough that 
it be easy to use -- it has to become widely adopted, at least among enough of 
the population that assuming easy key exchange, it would become a non-event for 
someone to send or receive an encrypted message. It would have to definitely be 
widespread enough that, if we also assume pervasive surveillance -- at least on 
a passive filtering level of some kind -- that to see cyphertext being 
transmitted back and forth would be common enough that it wouldn't raise alarms 
or attract attention of any sort. 

Let's get real -- assuming surveillance is the new normal, isn't it more likely 
that cyphertext in the datastream is -- at least as of this day and time -- 
more likely to attract attention from authorities than say, quality 
steganography or something like a carefully designed and well executed book 
code? 

Maybe the idea of pervasive surveillance and any resulting discomfort will 
raise interest in easy encryption among the general public, but given the state 
of the current crypto toolbox, I doubt it. 

Andrew

**for those who are PC-inclined, please note I use his alone not out of 
misogyny but for brevity and clarity. 


On Jun 11, 2013, at 9:56 PM, Kate Krauss ka...@critpath.org wrote:

 It's really easy to use these tools if you already know how to do it. 
 
 Otherwise they are often complicated and unintuitive. For some of us, they 
 represent an academic field or a fascinating hobby. For others, they are the 
 keys to survival.  Hubris--and not really caring whether they work or not for 
 non-geeks--is an obstacle to security.
 
 Most activists and journalists don't care how interesting these tools are, as 
 long as they can get them to work. If they were as simple and stupid as AOL 
 circa 2000, that would be great. 
 
 This is the beauty of cryptoparties--people can sit next to you and talk you 
 through it. Thanks, Asher Wolf. That is often all it takes. Otherwise, tiny 
 glitches or misunderstandings can put them out of reach.
 
 A security workshop my group organized a couple years ago included lots of 
 geeks ANDS lots of on-the-ground activists (of many stripes, including 
 

Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Paul Bernal (LAW)
This all rings very true for me: I'm a legal academic, and barely a geek, and 
in reality I barely ever use crypto. I was at the Privacy Law Scholars 
Conference in Berkeley last week when the PRISM story broke, and we had a 
special session at the end of the conference to talk about what we knew - and 
someone asked about 'user-friendly crypto' and there was a kind of laugh/cheer 
around the room. Everyone knows we want it, no-one believes it's there.

Paul

On 12 Jun 2013, at 09:27, Andy Isaacson a...@hexapodia.org wrote:

 On Tue, Jun 11, 2013 at 07:11:49PM -0700, Gregory Maxwell wrote:
 On Tue, Jun 11, 2013 at 6:56 PM, Kate Krauss ka...@critpath.org wrote:
 It's really easy to use these tools if you already know how to do it.
 
 I've been using PGP since 1994, if not earlier. In more recent times
 
 1998, here.
 
 it's become a regular part of my workflow in discussing security
 critical bugs. I am a programmer and a computing expert.
 
 I use gnupg daily.
 
 I do not consider the tools easy to use at all ...
 
 I routinely, and frequently, still get bitten by design bugs,
 implementation bugs, and UI bugs which continue to make the PGP
 ecosystem effectively unusable.  I cannot recommend PGP for routine use
 to anyone outside of the security community, and I don't think I know
 anyone who has used it consistently for more than 2 years without
 encountering a serious data/comms loss due to PGP bugs or gotchas.
 
 -andy
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Eugen Leitl
On Wed, Jun 12, 2013 at 06:15:30AM -0400, Sheila Parks wrote:
 Why not use her instead of his?
 
 Using his in 2013 is, indeed,  misogyny

List moderator, please control this before it completely goes out of hand.

People are trying to get work done here, and this is not helping.
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Guido Witmond

warning: plugging my wares [1] (again).


On 12-06-13 10:05, Andrew Feinberg wrote:


What exists is godawful at worse and cumbersome at best.

For a cryptosystem to really, and I mean really become widespread enough
to make an impact, it needs to be designed and implemented in such a way
that a given user who wants to add that level of security to his** email
need only install at the very least some manner of plugin to an existing
client, or at most switch to an easy to use replacement which has that
functionality built in seamlessly. Key exchange would have to be as easy
as forming connections on a social network. Heck, a crypto-social
network might be the best way to jump-start such a thing.


plugI've come up with something that might fit your requirements.

Technobabble: Users can create an cryptographic identity at the click of 
the mouse. With the verification methods I describe at the project site, 
it allows for man in the middle detection and prevention. His user agent 
takes care of all the crypto-details.


User sees: he creates an account at a (web) site by requesting an 
account name to be his. No need for email addresses, or identity 
validation that CA's do.


You can test it by downloading (or compiling) the user agent [2] and 
contact me at 'guidow@@dating.wtmnd.nl'. [3]

/plug



But let's be honest here -- I think we all are aware on some level or
another that even if one was able to develop and deploy the easiest
software imaginable (say, Apple's iCrypt that they'd allowed to be
vetted, even made key parts open source) and the most robust algorithms
known to man, it's not enough that it be easy to use -- it has to become
widely adopted, at least among enough of the population that assuming
easy key exchange, it would become a non-event for someone to send or
receive an encrypted message. It would have to definitely be widespread
enough that, if we also assume pervasive surveillance -- at least on a
passive filtering level of some kind -- that to see cyphertext being
transmitted back and forth would be common enough that it wouldn't raise
alarms or attract attention of any sort.


That's the problem, I'm facing, getting the initial seed planted.



Let's get real -- assuming surveillance is the new normal, isn't it more
likely that cyphertext in the datastream is -- at least as of this day
and time -- more likely to attract attention from authorities than say,
quality steganography or something like a carefully designed and well
executed book code?

Maybe the idea of pervasive surveillance and any resulting discomfort
will raise interest in easy encryption among the general public, but
given the state of the current crypto toolbox, I doubt it.


I hope so too. The Tor datastream is easy to recognize amidst the sea of 
plain text connections.


plugwith my plan, most connections are encrypted so those that need to 
rely on Tor have at least a better chance of hiding it.

/plug

Besides, with my protocol you really need Tor to protect your 
cryptographic identities against traffic analysis. Otherwise you're 
still fair game for the spooks.



Guido.

[1] my wares are found at http://eccentric-authentication.org/
[2] 
http://eccentric-authentication.org/blog/2013/06/07/run-it-yourself.html
[3] http://dating.wtmnd.nl:10443/aliens   (from within the proxied 
browser session).

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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Nadim Kobeissi
On 2013-06-12, at 6:20 AM, Eugen Leitl eu...@leitl.org wrote:

 On Wed, Jun 12, 2013 at 06:15:30AM -0400, Sheila Parks wrote:
 Why not use her instead of his?
 
 Using his in 2013 is, indeed,  misogyny
 
 List moderator, please control this before it completely goes out of hand.

+1

NK

 
 People are trying to get work done here, and this is not helping.
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread David Miller
On 12 June 2013 11:15, Sheila Parks sheilaruthpa...@comcast.net wrote:

  Why not use her instead of his?

What, in the phrase Glenn Greenwald had to substantially delay his
communications  ?

Surprised you got so many bites.

It's not even very high quality trolling :)

-- 
Love regards etc

David Miller
http://www.deadpansincerity.com
07854 880 883
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread The Doctor
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 06/11/2013 09:56 PM, Kate Krauss wrote:

 This is the beauty of cryptoparties--people can sit next to you and
 talk you through it. Thanks, Asher Wolf. That is often all it
 takes.

I think it's time for another wave of cryptoparties.

- -- 
The Doctor [412/724/301/703] [ZS]
Developer, Project Byzantium: http://project-byzantium.org/

PGP: 0x807B17C1 / 7960 1CDC 85C9 0B63 8D9F  DD89 3BD8 FF2B 807B 17C1
WWW: https://drwho.virtadpt.net/

What does it do?  How well does it do it? --Sean Kennedy

-BEGIN PGP SIGNATURE-
Version: GnuPG v2.0.20 (GNU/Linux)
Comment: Using GnuPG with Thunderbird - http://www.enigmail.net/

iEYEARECAAYFAlG4lsYACgkQO9j/K4B7F8HsEACg23MSzO17Soz8PPotj5C5fHaW
8pAAn1IS/P6c/mrAWZ31zFCDi4hpZPbO
=jJt1
-END PGP SIGNATURE-
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Eleanor Saitta
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA256

On 2013.06.12 11.54, micah wrote:
 I'm constantly hearing from people who complain about the UI in
 things like gnupg. I feel your pain, I do not want to argue that
 you are wrong. However, I do want to argue that complaining doesn't
 help to solve the problem. I've asked every single person who has
 complained about this problem to me recently, have you filed a bug
 about your issues? and everyone's response is: no.
 
 I've done this, and guess what? It works! I filed bugs and had 
 discussions on the gnupg mailing list that have made your
 experience with that tool a little bit better. There are many ways
 that I think it can be improved still, don't get me wrong, but the
 gnupg developers are reasonable people who want to make the
 software better, and probably have been hearing these complaints
 for years and years and would welcome a way to make people stop
 complaining.
 
 It seems there are a lot of people out there who have a clear idea
 of what is good and what is bad UI and are pretty vocal about when 
 something is bad. How about turning that into clear bugs that
 describe better workflow and UI? You dont have to be a crypto nerd,
 or a C programmer to make this stuff better and easier to use.

Is there any point in filing a bug that says Please have a
professional designer re-work all use flows in this system from
scratch?  (No.)  Is there any point in filing a bug that says Please
remove features X, Y, Z, Q, R, N, and M because they're too confusing
for novice users?  (No, especially when X is the entire web of
trust.)  Filing bugs isn't enough -- it's an entire design effort.
 Individuals may see a thing and think hey, this could be changed,
but what's needed is a top-to-bottom redesign, and that does not
translate into a simple set of clear bugs.  I don't believe that the
GPG designers have the resources available to do this design effort as
it stands, and it's not just them, it's the entire ecosystem that
needs to be involved and work together.

We'd love to see this fixed.  If it was this easy, it would have been
done years ago.

E.

- -- 
Ideas are my favorite toys.
-BEGIN PGP SIGNATURE-
Version: GnuPG v2.0.17 (MingW32)

iF4EAREIAAYFAlG4nLkACgkQQwkE2RkM0wpFNAD9Ez3mXSJRDrU5ViXz7+k1xbdd
iObK9CUbmIpPTmL+BoUA/315DpJFjW4FbO5L2yyTAix7X2QuV7UTzYaX4/XwZHF6
=nDoe
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Jonathan Wilkes





 From: micah mi...@riseup.net
To: Andy Isaacson a...@hexapodia.org; liberationtech 
liberationtech@lists.stanford.edu 
Sent: Wednesday, June 12, 2013 11:54 AM
Subject: Re: [liberationtech] Guardian reporter delayed e-mailing NSA source 
because crypto is a pain
 


Andy Isaacson a...@hexapodia.org writes:
 I use gnupg daily.

So do I, and you might too, and do not realize it! If you use Debian, a
Debian derivative (like Ubuntu), you use this stuff all the time, and
don't even have to think about it. 

 I do not consider the tools easy to use at all ...

When you talk about how hard this stuff is, and how unusable it is,
don't forget that there are cases where it is so easy and usable that
you are not even aware of it. 

Don't forget, however, that both users and devs of Debian can essentially
ignore the finer details of GPG because of the way the Debian community
itself operates.

Because freely available, freely auditable software is the product around
which the community is based, and because the Debian community itself
is made up of an unusually (uniquely?) high proportion of software mavens,
GPG web of trust can be leveraged to lower the cost of maintaining a
decentralized repository for the code/binaries.  If shenanigans happen,
the result (if any) will be evident in changed code/binary, which has a
history and can be changed back; moreover, since the entire community
is highly educated, even the laziest dev will quickly get up to speed if his/her
key turns out to be comprimised.

If we're going to refer to Debian in this context, it should
be as shining example of what can be achieved when there's a critical
mass of community members who know what their strengths are and
use them to make a system better than it was when they found it, and
give those improvements freely to everyone.  If you remove free
software as the core goal and replace it with Bitcoin OTC,
community credits or even free software equivalent of Facebook's
Like button, then you must reassess every single benefit that
web of trust has in Debian.  (E.g., there's no risk of credit default swaps
with free software.)

-Jonathan
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-12 Thread Brian Conley
+1 Micah

+1 Jillian Anne and Paul.
On Jun 12, 2013 7:24 PM, micah mi...@riseup.net wrote:

 Eleanor Saitta e...@dymaxion.org writes:

  -BEGIN PGP SIGNED MESSAGE-
  Hash: SHA256
 
  On 2013.06.12 11.54, micah wrote:
  I'm constantly hearing from people who complain about the UI in
  things like gnupg. I feel your pain, I do not want to argue that
  you are wrong. However, I do want to argue that complaining doesn't
  help to solve the problem. I've asked every single person who has
  complained about this problem to me recently, have you filed a bug
  about your issues? and everyone's response is: no.
 
  I've done this, and guess what? It works! I filed bugs and had
  discussions on the gnupg mailing list that have made your
  experience with that tool a little bit better. There are many ways
  that I think it can be improved still, don't get me wrong, but the
  gnupg developers are reasonable people who want to make the
  software better, and probably have been hearing these complaints
  for years and years and would welcome a way to make people stop
  complaining.
 
  It seems there are a lot of people out there who have a clear idea
  of what is good and what is bad UI and are pretty vocal about when
  something is bad. How about turning that into clear bugs that
  describe better workflow and UI? You dont have to be a crypto nerd,
  or a C programmer to make this stuff better and easier to use.
 
  Is there any point in filing a bug that says Please have a
  professional designer re-work all use flows in this system from
  scratch?  (No.)

 I agree, there is not much point in that.

  Is there any point in filing a bug that says Please remove features
  X, Y, Z, Q, R, N, and M because they're too confusing for novice
  users?  (No, especially when X is the entire web of trust.)

 I somewhat disagree with you on this point. There is a point to filing a
 bug that says, Please remove the choice of RSA/DSA/Elgamal from the gpg
 --gen-key process and just automatically use the default unless the user
 has passed --advanced. It is confusing for a user who is just learning
 to use the tool to have to make this choice.

  Filing bugs isn't enough -- it's an entire design effort.

 I do not think that it is one or the other. Don't throw out the bugs or
 usability enhancements because you think that the whole thing needs to
 be redesigned.

  Individuals may see a thing and think hey, this could be changed,
  but what's needed is a top-to-bottom redesign, and that does not
  translate into a simple set of clear bugs.  I don't believe that the
  GPG designers have the resources available to do this design effort as
  it stands, and it's not just them, it's the entire ecosystem that
  needs to be involved and work together.

 I disagree. I've been working with people who have been doing this sort
 of iterative changes with the software for years and things have gotten
 better.

 It is actually not that hard to make significant usability changes
 without needing to make top-to-bottom changes.

 For example, here is a bug I filed which coalesces my experiences doing
 gnupg trainings with different activists and the stumbling blocks that
 we ran into:


 https://bugs.g10code.com/gnupg/issue1506?@ok_message=msg%204634%20created%0Aissue%201506%20created@template=item

  We'd love to see this fixed.  If it was this easy, it would have been
  done years ago.

 You would be surprised the changes that you can get if you ask for
 them and describe clearly why they are needed. It helps a lot if you can
 also clearly describe a better alternative. If you know how to code and
 have time, then providing a patch will go even further. Although patches
 are always welcome, they are not required.

 For a really long time, smart cryptographers have been writing this
 software, their heads are focused on doing the correct technical thing
 and that doesn't always translate into an easy experience. They have
 been doing this so long that they cannot see how this could be any
 different. It is up to us who aren't so deeply stewed in hashing
 algorithms and trust metrics, we who work with people who provide us the
 feedback who can synthesize it and bring that back to those people in
 who know the code so that they can make it more usable.

 If we do not do that, it will not happen, ever. No matter how much we
 complain in places where they will never hear us.

 My experience has been that software gets better when I point out the
 problems to the appropriate place that the developers have asked for
 those things to be put. Sometimes that takes several years, sometimes I
 get lucky and the change happens in a weekend. It very rarely gets
 better on its own.

 You may think that the whole crypto world needs to be thrown out and we
 need to start again, and you see that as an intractably impossible
 problem. I see things differently because I've seen annoying things
 iteratively become usable over time, and I've seen usable 

[liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-11 Thread Nadim Kobeissi
This story really solidifies why I believe that we need to make privacy 
technologies accessible to journalists, instead of simply focusing on the other 
way around.

Glenn Greenwald had to substantially delay his communications with Edward 
Snowden due to how inaccessible a lot of privacy and encryption software is to 
use.

Our main and primary goal at Cryptocat has been to focus on making encrypted 
communications accessible, easier to use and fun and attractive. We've always 
believed that accessibility is a security feature, and this idea is at the core 
of our project.

http://arstechnica.com/security/2013/06/guardian-reporter-delayed-e-mailing-nsa-source-because-crypto-is-a-pain/

NK
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Re: [liberationtech] Guardian reporter delayed e-mailing NSA source because crypto is a pain

2013-06-11 Thread Gregory Maxwell
On Tue, Jun 11, 2013 at 6:56 PM, Kate Krauss ka...@critpath.org wrote:
 It's really easy to use these tools if you already know how to do it.

I've been using PGP since 1994, if not earlier. In more recent times
it's become a regular part of my workflow in discussing security
critical bugs. I am a programmer and a computing expert.

I do not consider the tools easy to use at all but I understand their
importance and use them with other people who understand their
importance, _in spite_ of the fact that they are burdensome. I am
large unable to get people who do not understand their importance to
use them. Or even if I get them to use them once, because the tools
require an effort to use on an ongoing basis they do not use them
reliably.

The only shining ray of success I've experienced in this space is OTR,
and but my personal experience is that even that is failing as more
people move away from using pidgin and adium to chat systems which OTR
does not as easily integrate with.
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