[cryptography] why did OTR succeed in IM?

2013-03-23 Thread ianG

Someone on another list asked an interesting question:

 Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?



(The reason this is interesting (to me?) is that there are not so many 
instances in our field where there are open design competitions at this 
level.  The results of such a competition can be illuminating as to what 
matters and what does not.  E.g., OpenPGP v. S/MIME and SSH v. secure 
telnet are two such competitions.)




iang
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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Guido Witmond

On 03/23/2013 10:25 AM, ianG wrote:

Someone on another list asked an interesting question:




Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?



I find that interesting too. What list would that be?

Guido.

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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Ben Laurie
On 23 March 2013 09:25, ianG i...@iang.org wrote:
 Someone on another list asked an interesting question:

  Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?

Because Adium built it in?




 (The reason this is interesting (to me?) is that there are not so many
 instances in our field where there are open design competitions at this
 level.  The results of such a competition can be illuminating as to what
 matters and what does not.  E.g., OpenPGP v. S/MIME and SSH v. secure telnet
 are two such competitions.)



 iang
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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Peter Saint-Andre
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On 3/23/13 7:36 AM, Ben Laurie wrote:
 On 23 March 2013 09:25, ianG i...@iang.org wrote:
 Someone on another list asked an interesting question:
 
 Why did OTR succeed in IM systems, where OpenPGP and x.509 did
 not?
 
 Because Adium built it in?

In the early Jabber days, we had OpenPGP support in several clients
such as Gabber, Psi, and WinJab. Although such clients could have
created special-purpose PGP keys, in practice the perception was that
OpenPGP was hard, that people would use existing keys, that Aunt
Tillie would never have a PGP key, etc. It didn't help that (IIRC)
GnuPG made some breaking API changes or somesuch around 2001 that
annoyed various Jabber client developers.

When we standardized the core Jabber protocol as XMPP at the IETF in
2003-2004, the working group settled on using X.509 for various
not-so-good reasons related to IETF politics at the time, resulting in
the monstrosity known as RFC 3923. (And we all know how well
client-side X.509 certificates have worked out.)

IMHO, there are three main reasons why OTR succeeded:

1. It worked across all IM systems.

2. It was relatively friendly for end users, compared to OpenPGP and
X.509.

3. It was built into the most popular open-source IM clients (Pidgin
and Adium).

Peter

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Peter Saint-Andre
https://stpeter.im/


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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Jon Callas
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On Mar 23, 2013, at 6:36 AM, Ben Laurie b...@links.org wrote:

 On 23 March 2013 09:25, ianG i...@iang.org wrote:
 Someone on another list asked an interesting question:
 
 Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?
 
 Because Adium built it in?
 

Yeah. And it just worked. It took me two hours to find a Jabber client that 
actually worked (Psi) and get Psi working with OpenPGP support, and even then 
it was just weird, from a UX perspective.

But there's also one other thing, and that is that there was no other real 
competitor. So:

* Greenfield advantage
* Better UX
* Better out-of-the-box experience.

Jon




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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Ben Laurie
On 23 March 2013 16:51, Peter Saint-Andre stpe...@stpeter.im wrote:
 3. It was built into the most popular open-source IM clients (Pidgin
 and Adium).

It isn't actually built in to Pidgin. Should be, IMO.
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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread Nico Williams
On Saturday, March 23, 2013, ianG wrote:

 Someone on another list asked an interesting question:

  Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?


Because it turns out that starting with anonymous key exchange is good
enough in many cases.  Leap of faith would have been a good addition, but
would have created device sync issues, and the answer/question
authentication is good enough.  Imagine if we'd insisted on a PKI for IM...
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Re: [cryptography] why did OTR succeed in IM?

2013-03-23 Thread James A. Donald

On 2013-03-24 3:25 AM, Jon Callas wrote:

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On Mar 23, 2013, at 6:36 AM, Ben Laurie b...@links.org wrote:


On 23 March 2013 09:25, ianG i...@iang.org wrote:

Someone on another list asked an interesting question:

 Why did OTR succeed in IM systems, where OpenPGP and x.509 did not?

Because Adium built it in?


Yeah. And it just worked.



The hard part of cryptography is always UI.
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