Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-15 Thread Richard

On Wed, Aug 14, 2013 at 07:12:24PM -0400, Tom Ritter wrote:

On 14 August 2013 18:01, Richard r...@linux-m68k.org wrote:
 On the other end of the paranoia scale I would like to remind folks of the
 the mixmaster remailer chaining technique which does much more than plain
 encryption - as far as I can see it is theoretically completely untraceable.

That statement is not correct.  Mix networks require more effort to
trace than normal packets or Onion Routing, but are not even close to
theoretically completely untraceable.  I'll point to Syverson's
papers (Why I'm not an entropist, and Sleeping dogs lie in a bed of
onions) and Serjantov's From a Trickle to a Flood.


thanks for the pointers, will review them when I have time. 


Still think that mixmaster would deserve more attention.


Richard

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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-14 Thread Tom Ritter
On 9 August 2013 18:16, Seth David Schoen sch...@eff.org wrote:
 If you think governments are likely to use their own CAs for spying by
 issuing fraudulent certificates, you want to remove trust for those
 CAs _in your web browser_.  Having a valid, correct, and publicly issued
 certificate from such a CA does not make the CA operator any more able
 to spy on you.

 There was a lot of concern when CNNIC became a root CA in mainstream
 browsers because of the perception that the Chinese government could
 force CNNIC to misissue certificates to facilitate surveillance.  But
 this risk would be a reason for users not to trust the CNNIC root in
 their browsers, not directly a reason for sites to avoid getting certs
 from CNNIC.

While I agree your technical assessment is correct, I do want to note
(and you'll probably agree with me) that if you think a CA may
misissue/rollover for a government, the (indirect) reasons not to buy
from that CA are to a) not give them additional money and b) reduce
the number of certs on the internet using that CA, making it
ever-so-slightly more possible for browsers will eventually be able to
remove it from their trust stores.

Aside from StartCom (free) most CAs have roughly the same price and
service.  Since service is equivalent, you're free to choose a CA
based on your political opinion, and not worry about missing out on
'features'. It's basically like voting in an election - elections are
won by tens or hundreds of thousands of votes, so it seems like one
vote doesn't matter.  But it can add up.

-tom
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-14 Thread Ralph Holz
Hi Tom

 Aside from StartCom (free) most CAs have roughly the same price and
 service.  Since service is equivalent, you're free to choose a CA
 based on your political opinion, and not worry about missing out on
 'features'. It's basically like voting in an election - elections are
 won by tens or hundreds of thousands of votes, so it seems like one
 vote doesn't matter.  But it can add up.

Not sure if you know this one, but this article paints a somewhat more
complex picture of the HTTPS economics. In particular, companies buy
from the big players because, alas and behold, they're too big to fail
and will never be removed from root stores:

@INPROCEEDINGS{Asghari2013,
  author = {Asghari, Hadi and van Eeten, Michel J. G. and Arnbak, Axel
M. and van Eijk, Nico A. N. M.},
  year = {2013},
  month = {March},
  title = {Security Economics in the {HTTPS} value chain},
  location = {Washington, D.C., USA},
  booktitle = {Proc. 12th Ann. Workshop on the Economics of Information
Security (WEIS 2013)},
}

Ralph


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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-14 Thread Tom Ritter
On 14 August 2013 18:01, Richard r...@linux-m68k.org wrote:
 On the other end of the paranoia scale I would like to remind folks of the
 the mixmaster remailer chaining technique which does much more than plain
 encryption - as far as I can see it is theoretically completely untraceable.

That statement is not correct.  Mix networks require more effort to
trace than normal packets or Onion Routing, but are not even close to
theoretically completely untraceable.  I'll point to Syverson's
papers (Why I'm not an entropist, and Sleeping dogs lie in a bed of
onions) and Serjantov's From a Trickle to a Flood.



On 14 August 2013 10:17, Ralph Holz h...@net.in.tum.de wrote:
 Hi Tom

 Aside from StartCom (free) most CAs have roughly the same price and
 service.  Since service is equivalent, you're free to choose a CA
 based on your political opinion, and not worry about missing out on
 'features'. It's basically like voting in an election - elections are
 won by tens or hundreds of thousands of votes, so it seems like one
 vote doesn't matter.  But it can add up.

 Not sure if you know this one, but this article paints a somewhat more
 complex picture of the HTTPS economics. In particular, companies buy
 from the big players because, alas and behold, they're too big to fail
 and will never be removed from root stores:

 @INPROCEEDINGS{Asghari2013,
   author = {Asghari, Hadi and van Eeten, Michel J. G. and Arnbak, Axel
 M. and van Eijk, Nico A. N. M.},
   year = {2013},
   month = {March},
   title = {Security Economics in the {HTTPS} value chain},
   location = {Washington, D.C., USA},
   booktitle = {Proc. 12th Ann. Workshop on the Economics of Information
 Security (WEIS 2013)},
 }


I had not seen that paper, that's cool thanks.  However, it seems
they're observing data (EFF Observatory and Market Prices) and drawing
conclusions about why companies make decisions.  It would be easier
and more reliable to just... ask the companies why they do what they
do.  They seem to omit that somewhat important step to support their
conclusions.

-tom
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-10 Thread Ali-Reza Anghaie
Griffin,

The more this gets fleshed out on list - the more it departs from any
vestige of email and then you're basically talking about shoe-horning
a different architectural beast into a transport protocol we happen to
know. (I'm not saying ~you~ are planning that - just making an
observation of nuanced list evolution.)

You're going to end up in a place that it might be more tenable to
pursue building out better transport options for a RetroShare or Kolab
environment. Usability for new users is going to take a massive hit
with any proposal that seems to catch interest above. I therefore I
think it may be prudent to consider an encapsulated secure environment
(using RetroShare as an example) with a bridge ingress/egress to the
outside world services that gets handled like a PGP Universal setup.
Using x509 or PGP, not sure we'd care as long as the CA model of today
had nothing to do with it - or minimally involved in the external
bridging.

In a sense what I'm saying is stop even considering secure email an
option - we need to start having people think about their
communications and security models entirely different. And I'm afraid
that even attempting to maintain vestiges of the old environment and
~terminology~ actually does more harm than good.

This isn't to say abandon security of email - but lets tackle the
new-fangled solutions on one leg (leaving behind as much legacy as
possible) - and use political means to continue to attack the
Internet of old problems (e.g. email) on the other leg.

That made total sense in my head. *grimace* Cheers, -Ali
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-10 Thread Richard
On Fri, Aug 09, 2013 at 05:07:26PM -0400, Tim Prepscius wrote:
 If you'd like to help me that would be cool..
 
 My take on this is this:  (these are are not all my ideas, can't take
 full credit)
 
 
 We want to get to a state where an e-mail server is easy to set up.
 And runs with *non governmental* issued ssl certificates.
 Where it provides web-mail (think gmail), iPhone and android.

how do you make webmail with PGP end to end encryption? I assume you
could do PGP in javascript but it would be trivially easy for the server
to steal the users secret keys in that case.


Richard

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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread Hans of Guardian

I think there would be some value to a system like that.  It would address a 
lot of real world threats but it will not address large scale government 
monitoring systems, which many governments have (US, China, UK, Iran, etc).

Sounds like you should team up with Tim Prepscius with his system that he's 
been posting about here.

.hc

On Aug 9, 2013, at 2:07 PM, Griffin Boyce wrote:

  This probably sounds very strange, but *what if* someone ran an email
 service that required that all mails be GPG encrypted?
 
  So here's my idea: Barring the honor system, it would require a filter
 to look at message content to check for PGP headers.  And if said
 headers didn't exist, the message doesn't get sent.[1] There's no Sent
 Mail folder on the server, so if you want a copy, you'd need to have
 Thunderbird (etc) set up to store them locally.
 
  It wouldn't protect from metadata collection, but it would at least
 (to some extent) protect people from their own poor security decisions
 while emphasizing that options exist to protect themselves.
 
 Considerations:
* This assumes that an order would arrive to disable PGP filter and
 enable a sent folder (eg, this idea assumes metadata is unprotected)
 
* Those playing at home may recognize this as a naive Bayes
 classifier, given that the presence of PGP headers don't necessarily
 mean the actual message is encrypted. There are other (heavier) steps
 that could be taken, like checking for encryption on outbound with SJCL,
 but I think that probability is on our side here.
 
* In the face of an NSL, the service would realistically either fall
 back to policy (removing tech-based enforcement by order) or shut down
 entirely.
 
  What does everyone think? Is this totally nuts or what?
 
 best,
 Griffin
 
 -- 
 Cypherpunks write code not flame wars. --Jurre van Bergen
 #Foucault / PGP: 0xAE792C97 / OTR: sa...@jabber.ccc.de
 mailto:sa...@jabber.ccc.de
 
 My posts, while frequently amusing, are not representative of the
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread Tim Prepscius
If you'd like to help me that would be cool..

My take on this is this:  (these are are not all my ideas, can't take
full credit)


We want to get to a state where an e-mail server is easy to set up.
And runs with *non governmental* issued ssl certificates.
Where it provides web-mail (think gmail), iPhone and android.



The meta data problem goes away if the point of failure is spread thin enough.
Basically, you rely that the NSA will not take the chance of sending a
secret order to 1000 people with consciences.
If everyone is using non government issued ssl certificates, the
XKeyscore problem goes away.
(only a guess though of course)



The mail client will have pgp mime end-to-end.
The mail server, run by you, or run by a friend of yours, or some
business, will provide a secure means to login for web-mail.


..

What I'm doing is:

1. finishing off getting all of the source on github
2. this weekend work on deploying easily to an ec2 instance.

If you'd like to help, you could get it from github
https://github.com/timprepscius/mailiverse

and try to build things, see what breaks, although I'm sure I'll find
out on my own pretty soon.


If you have any expertise in PGP mime, I could use it.  Setting up PGP
mime looks like it will be trivial.  I just have to figure out what to
do.  Which takes longer than writing the code unfortunately.

-tim




On 8/9/13, Hans of Guardian h...@guardianproject.info wrote:

 I think there would be some value to a system like that.  It would address a
 lot of real world threats but it will not address large scale government
 monitoring systems, which many governments have (US, China, UK, Iran, etc).

 Sounds like you should team up with Tim Prepscius with his system that he's
 been posting about here.

 .hc

 On Aug 9, 2013, at 2:07 PM, Griffin Boyce wrote:

  This probably sounds very strange, but *what if* someone ran an email
 service that required that all mails be GPG encrypted?

  So here's my idea: Barring the honor system, it would require a filter
 to look at message content to check for PGP headers.  And if said
 headers didn't exist, the message doesn't get sent.[1] There's no Sent
 Mail folder on the server, so if you want a copy, you'd need to have
 Thunderbird (etc) set up to store them locally.

  It wouldn't protect from metadata collection, but it would at least
 (to some extent) protect people from their own poor security decisions
 while emphasizing that options exist to protect themselves.

 Considerations:
* This assumes that an order would arrive to disable PGP filter and
 enable a sent folder (eg, this idea assumes metadata is unprotected)

* Those playing at home may recognize this as a naive Bayes
 classifier, given that the presence of PGP headers don't necessarily
 mean the actual message is encrypted. There are other (heavier) steps
 that could be taken, like checking for encryption on outbound with SJCL,
 but I think that probability is on our side here.

* In the face of an NSL, the service would realistically either fall
 back to policy (removing tech-based enforcement by order) or shut down
 entirely.

  What does everyone think? Is this totally nuts or what?

 best,
 Griffin

 --
 Cypherpunks write code not flame wars. --Jurre van Bergen
 #Foucault / PGP: 0xAE792C97 / OTR: sa...@jabber.ccc.de
 mailto:sa...@jabber.ccc.de

 My posts, while frequently amusing, are not representative of the
 thoughts of my employer.
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread Richard
On Fri, Aug 09, 2013 at 02:07:25PM -0400, Griffin Boyce wrote:
   This probably sounds very strange, but *what if* someone ran an email
 service that required that all mails be GPG encrypted?

I did long wish for a system that would send every non-GPG message
to the spamfolder.

Richard

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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread David Holl
ooh, I love this discussion.  I'll drop in my quick points, and would love to 
hear other perspectives.

2 points:

1)  Is there a milter that could be plugged into existing SMTP servers 
(sendmail, postfix, ...) that could require OpenPGP encapsulation, and 
immediately reject messages back to the sender upon receipt of unprotected 
email.  (Heck, maybe the message doesn't even have to be signed or encrypted 
but just require the minimum that has either the proper PGP mime encapsulation 
or an inline-format ascii armored format.)

If such a milter does not exist, we could create one.  Being a milter means 
this code could be plugged into a variety of existing SMTP servers that are 
already deployed.


2)  Sorry, but isn't any mail service that runs a web front-end subject to its 
country's government stepping in and requiring backdoors or other means of 
tampering with the web code that's sent to customer's browsers?  (ie, is there 
any technical reason that a web-based email provider could not comply with a 
secret order to insert backdoors into code sent from centrally controlled web 
servers to the clients?)

Heck, even downloading apps off Google Play doesn't feel secure.  It is 
technically feasible that Google could comply with a court order to inject a 
backdoor into a third-party's app (or their own app) for when only 1 user's 
phone automatically probes the play service for updates.  (It sounds far 
fetched, yes.  But it is technically feasible, and many things sound far 
fetched until we later find out it has been true for a while.)

Security (privacy) could only be had when you can trust your computing platform 
(must be personally owned and controlled), and that is pretty hard to 
guarantee.  (including baseband chipset backdoors, etc...)  However, just 
because something may be hard, doesn't mean we shouldn't strive for it.  :)


--- So in closing...

I figure just a milter that requires all traffic to be encapsulated via any 
format of PGP / OpenPGP / GNUPG / whateverPG would be a fantastic start.  But 
I'm not so sure about being able to give anyone security through any webmail 
clients.  (heaven forbid that anyone's webmail is actually served off of a VPS 
in the cloud somewhere... and thus subject to court orders given to the 
company providing the VPS service...)


- David  :)
(putting my tin foil hat back on and releasing the dolphins back to the ocean 
with my private keys...)


On Fri, Aug 09, 2013 at 05:07:26PM -0400, Tim Prepscius wrote:
 If you'd like to help me that would be cool..
 
 My take on this is this:  (these are are not all my ideas, can't take
 full credit)
 
 
 We want to get to a state where an e-mail server is easy to set up.
 And runs with *non governmental* issued ssl certificates.
 Where it provides web-mail (think gmail), iPhone and android.
 
 
 
 The meta data problem goes away if the point of failure is spread thin enough.
 Basically, you rely that the NSA will not take the chance of sending a
 secret order to 1000 people with consciences.
 If everyone is using non government issued ssl certificates, the
 XKeyscore problem goes away.
 (only a guess though of course)
 
 
 
 The mail client will have pgp mime end-to-end.
 The mail server, run by you, or run by a friend of yours, or some
 business, will provide a secure means to login for web-mail.
 
 
 ..
 
 What I'm doing is:
 
 1. finishing off getting all of the source on github
 2. this weekend work on deploying easily to an ec2 instance.
 
 If you'd like to help, you could get it from github
 https://github.com/timprepscius/mailiverse
 
 and try to build things, see what breaks, although I'm sure I'll find
 out on my own pretty soon.
 
 
 If you have any expertise in PGP mime, I could use it.  Setting up PGP
 mime looks like it will be trivial.  I just have to figure out what to
 do.  Which takes longer than writing the code unfortunately.
 
 -tim
 
 
 
 
 On 8/9/13, Hans of Guardian h...@guardianproject.info wrote:
 
  I think there would be some value to a system like that.  It would address a
  lot of real world threats but it will not address large scale government
  monitoring systems, which many governments have (US, China, UK, Iran, etc).
 
  Sounds like you should team up with Tim Prepscius with his system that he's
  been posting about here.
 
  .hc
 
  On Aug 9, 2013, at 2:07 PM, Griffin Boyce wrote:
 
   This probably sounds very strange, but *what if* someone ran an email
  service that required that all mails be GPG encrypted?
 
   So here's my idea: Barring the honor system, it would require a filter
  to look at message content to check for PGP headers.  And if said
  headers didn't exist, the message doesn't get sent.[1] There's no Sent
  Mail folder on the server, so if you want a copy, you'd need to have
  Thunderbird (etc) set up to store them locally.
 
   It wouldn't protect from metadata collection, but it would at least
  (to some extent) protect people from their own poor security 

Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread Seth David Schoen
Tim Prepscius writes:

 We want to get to a state where an e-mail server is easy to set up.
 And runs with *non governmental* issued ssl certificates.

I think this might reflect a misperception of the threat model around
misissuance of certificates.

If you think governments are likely to use their own CAs for spying by
issuing fraudulent certificates, you want to remove trust for those
CAs _in your web browser_.  Having a valid, correct, and publicly issued
certificate from such a CA does not make the CA operator any more able
to spy on you.

There was a lot of concern when CNNIC became a root CA in mainstream
browsers because of the perception that the Chinese government could
force CNNIC to misissue certificates to facilitate surveillance.  But
this risk would be a reason for users not to trust the CNNIC root in
their browsers, not directly a reason for sites to avoid getting certs
from CNNIC.  The cert isn't some kind of poison for private
communications that use it, it's just a way of telling browsers that your
key is OK to use.  If you have a cert that tells browsers that your key
is OK to use and the browsers will accept it and you agree with the
contents of that cert, the cert is fine for you to use on your site.

The risk to me from, say, CNNIC is that even though I use a cert from
StartCom, CNNIC will secretly misissue a different cert for my site
containing a public key controlled by the Chinese government, and then
the government can use that to spy on some users who communicate with
my site.  The risk is not that I would ask CNNIC's CA for a cert for my
site containing my actual public key and that they would say yes and give
it to me. :-)

-- 
Seth Schoen  sch...@eff.org
Senior Staff Technologist   https://www.eff.org/
Electronic Frontier Foundation  https://www.eff.org/join
815 Eddy Street, San Francisco, CA  94109   +1 415 436 9333 x107
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Re: [liberationtech] [guardian-dev] An email service that requires GPG/PGP?

2013-08-09 Thread Tim Prepscius
I'd like to respond to this just a bit.

1.  requiring PGP without giving a user centric means of using PGP
doesn't actually solve anything.

It's like telling an adult they have to eat stinky tofu.  If they love
stinky tofu then fine, but if they don't, there is no way it's going
to happen.
I would guess that 0.01% of people LIKE the thunderbird experience.
Whereas I would guess 90% like gmail.

Also, getting people to download and install software is very
difficult these days.



2. web mail security:

I think web mail security can be better than you think.

What is necessary for security?  Code not being tampered with.
Can you verify code has not been tampered with?  Yes (up to a point of course).

Retrieval and protection of keys from a central server.
I believe my scheme is viable.  I believe there is no way for any
agency to do mass surveillance by cracking of tens of thousands of
keys to read e-mail.  It probably is possible to break a single user,
but nothing can protect a single user from the NSA/FBI/CIA.  (did
you recognize the utility man who came last time?  no?  well you might
have a key-logger, or a camera might be in your room)

I could be wrong of course, but if I'm wrong, I think someone will fix it.



3.  also, I think it is important to understand the limits of cloud
service back doors.

Let's say that you only used the cloud to store encrypted files.
And you used your own personal computer to run the mail server, static
ip proxy-ing off an ec2 instance.
(this is best I think).

it wouldn't matter if the cloud was a threat because everything is
encrypted anyways.
I mean wouldn't matter means, sort of wouldn't matter, there is
always meta data, file size, file write time, etc.


Ahh.. I see, I wrote that I was setting up the deploy to go to an ec2
instance.  This gave the wrong impression perhaps.
I don't have any free machines at the moment, and zero disk space
weirdly, so I'm going to use ec2 instances to test.


--

Anyways, super tired, hope my rambling isn't too incoherent.

Cheers,

-tim


On 8/9/13, David Holl da...@ad5ey.net wrote:
 ooh, I love this discussion.  I'll drop in my quick points, and would love
 to hear other perspectives.

 2 points:

 1)  Is there a milter that could be plugged into existing SMTP servers
 (sendmail, postfix, ...) that could require OpenPGP encapsulation, and
 immediately reject messages back to the sender upon receipt of unprotected
 email.  (Heck, maybe the message doesn't even have to be signed or encrypted
 but just require the minimum that has either the proper PGP mime
 encapsulation or an inline-format ascii armored format.)

 If such a milter does not exist, we could create one.  Being a milter
 means this code could be plugged into a variety of existing SMTP servers
 that are already deployed.


 2)  Sorry, but isn't any mail service that runs a web front-end subject to
 its country's government stepping in and requiring backdoors or other means
 of tampering with the web code that's sent to customer's browsers?  (ie, is
 there any technical reason that a web-based email provider could not comply
 with a secret order to insert backdoors into code sent from centrally
 controlled web servers to the clients?)

 Heck, even downloading apps off Google Play doesn't feel secure.  It is
 technically feasible that Google could comply with a court order to inject a
 backdoor into a third-party's app (or their own app) for when only 1 user's
 phone automatically probes the play service for updates.  (It sounds far
 fetched, yes.  But it is technically feasible, and many things sound far
 fetched until we later find out it has been true for a while.)

 Security (privacy) could only be had when you can trust your computing
 platform (must be personally owned and controlled), and that is pretty hard
 to guarantee.  (including baseband chipset backdoors, etc...)  However, just
 because something may be hard, doesn't mean we shouldn't strive for it.  :)


 --- So in closing...

 I figure just a milter that requires all traffic to be encapsulated via any
 format of PGP / OpenPGP / GNUPG / whateverPG would be a fantastic start.
 But I'm not so sure about being able to give anyone security through any
 webmail clients.  (heaven forbid that anyone's webmail is actually served
 off of a VPS in the cloud somewhere... and thus subject to court orders
 given to the company providing the VPS service...)


 - David  :)
 (putting my tin foil hat back on and releasing the dolphins back to the
 ocean with my private keys...)


 On Fri, Aug 09, 2013 at 05:07:26PM -0400, Tim Prepscius wrote:
 If you'd like to help me that would be cool..

 My take on this is this:  (these are are not all my ideas, can't take
 full credit)


 We want to get to a state where an e-mail server is easy to set up.
 And runs with *non governmental* issued ssl certificates.
 Where it provides web-mail (think gmail), iPhone and android.



 The meta data problem goes away if the point of failure