Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Michael Rogers
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

On 11/10/13 01:14, carlo von lynX wrote:
 No one anywhere has solved the problem of asynchronous,
 forward-secret group cryptography.
 
 I think you have to be a bit opportunistic about it. Briar does it
 somehow, if I understood correctly.

Yes and no. I think Elijah's referring to the problem of encrypting a
message to a group of recipients, so that any recipient can decrypt it
up until a certain time, and nobody can decrypt it after that. We
haven't solved that problem, but we do have a different solution for
asynchronous forward-secret group communication.

No crypto innovation is involved, it's just a matter of group members
disseminating the message over forward-secret pairwise links. I think
Retroshare might do the same... but who knows? ;)

Cheers,
Michael

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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Tempest
Gregory Maxwell:
 My other big technical complaint about PGP is (3) in the post, that
 every encrypted message discloses what key you're communicating with.
 PGP easily _undoes_ the privacy that an anonymity network like tor can
 provide.  It's possible to use --hidden-recipient but almost no one
 does.

i am often a bit confused as to why people take issue with the fact that
gpg/pgp isn't anonymous. i don't recall the technology ever being
proposed as such. rather, effort was made to have mechanisms to verify
the identity of a sender. however, if one creates an identity and
keypair that as only been used over tor, what's the problem? creating
and maintaining anonymity is an entirely different subject that gpg/pgp
was not created to address.

i'm going to have to cosign with jillian and others who took issue with
this list. i don't think it provided good reasons to not use gpg/pgp. in
fact, i struggled with figuring out what threat models the author was
addressing in the various points, as it jumped around a bit without
providing much detail. that lack of detail made the conclusion a bit
irresponsible.


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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Gregory Maxwell
On Fri, Oct 11, 2013 at 10:24 AM, Tempest temp...@tushmail.com wrote:
 Gregory Maxwell:
 My other big technical complaint about PGP is (3) in the post, that
 every encrypted message discloses what key you're communicating with.
 PGP easily _undoes_ the privacy that an anonymity network like tor can
 provide.  It's possible to use --hidden-recipient but almost no one
 does.

 i am often a bit confused as to why people take issue with the fact that
 gpg/pgp isn't anonymous. i don't recall the technology ever being
 proposed as such. rather, effort was made to have mechanisms to verify
 the identity of a sender. however, if one creates an identity and
 keypair that as only been used over tor, what's the problem? creating
 and maintaining anonymity is an entirely different subject that gpg/pgp
 was not created to address.

Security is a complicated subject. The exact properties you need to be
secure depend on your threat model.

You add encryption via PGP because you know you need encryption in
order to be secure against your threat model.  But without it being
very obvious PGP has written a long term identity fingerprint encoded
in the opaque base64 data which distinguishes your messages by
recipients.

This long term identity key can _increase_ your vulnerability to
traffic analysis over using nothing at all. It does so invisibly to
many users. It may be a very bad thing for your threat model.

I think communications security tools ought to avoid increasing
vulnerability to any common threats to the greatest extent that they
can, and when they must compromise they should make it obvious.

Both for non-repudiation and resistance to traffic analysis PGP
dramatically reduces user security and does so in a way which is not
obvious to any except the most advanced users. Both of these could be
fixed with basically no user impact: Make hidden-recipient the default
and allow optional clear-text recipient list on ascii armored output;
add an authentication mode which is used by default instead of
signing for encrypted messages that uses ring signatures (and don't
allow unauthenticated encryption, geesh).

 effort was made to have mechanisms to verify the identity of a sender

PGP actually has no mechanism for that. Thats authentication. Instead
PGP substitutes non-repudiation for that purpose, which is a superset
of authentication which reduces security in many situations.  PGP
provides basically no way for me to convince you that I'm the author
of a message without also making it possible for you to prove it to
the whole world. Sometimes you want this— for contracts and such— but
usually you just want authentication.

 if one creates an identity and keypair that as only been used over tor

Say you are a famous anonymous developer that creates software for
dissidents to help them connect to tor.  You have a nice anonymous key
that is well known to belong to you.

Do you think any of your users should want to send you email to
anonymous one time use tech support mailboxes using that key, provably
showing they were communicating to you to anyone who can monitor their
email?  Do you think your users will even realize that sending you
messages will expose them?
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Ali-Reza Anghaie
On Thu, Oct 10, 2013 at 3:23 PM, carlo von lynX
l...@time.to.get.psyced.org wrote:
 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.

I love the detail put into this but I think it's a poorly delivered
message for multiple reasons:

1) It puts an over-abundance of faith in toolsets in opening and
closing You have to get used to learning new software frequently.
Realistically if this was a toolsets problem then EFF and EPIC
wouldn't exist - it's not. It's a problem of State that can only be
fought through OPSEC, policy, and risk management. Since it's not
entirely reasonable to have end-users living the spook lifesystem then
it leaves ~policy~ as the best out for end-users with tools (like PGP)
being the defensive linemen.

2) Combined with (1) - then providing no immediate alternative - it
creates the environment in which snake oil fills the gaps. Then we're
back out fighting the snakeoil because we were too busy eating our
young (or old in this case) to pay attention to the collateral damage
to our end-users.

3) It groups multiple problem sets into the responsibilty domain of
PGP - when it/they don't have to be, perhaps even undesirable to be so
(from both technical and sociological viewpoints).

So in terms of broad proclamations I think it's prudent to keep those
at a policy level - and the rest behind transparent but loosely narrow
doors until the collective geekdom we can get traction on better
alternatives. -Ali
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Tempest
Gregory Maxwell:
 
 Do you think any of your users should want to send you email to
 anonymous one time use tech support mailboxes using that key, provably
 showing they were communicating to you to anyone who can monitor their
 email?  Do you think your users will even realize that sending you
 messages will expose them?

a fair point. but one could significantly address this issue by hosting
the public key on a tor hidden service. that would greater ensure that,
in order to get your key, they would be using a system that protects
against such threats. hardly an easy solution. but it can be solved
with a little extra planning.



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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-11 Thread Gregory Maxwell
On Fri, Oct 11, 2013 at 12:10 PM, Tempest temp...@tushmail.com wrote:
 a fair point. but one could significantly address this issue by hosting
 the public key on a tor hidden service. that would greater ensure that,
 in order to get your key, they would be using a system that protects
 against such threats. hardly an easy solution. but it can be solved
 with a little extra planning.

Of course, if you can do this and the HS is secure, then you can just
dispense with the PGP altogether.

You can work around the limitations I've pointed to here... You
messages via hidden services without pgp at all.. or you can create
per-recipient symmetric keys which you clearsign then encrypt with
hidden-recipent to each person you want to talk to, then symmetrically
encrypt your actual messages, and discard once a conversation is done.

But no one does, because it's hard, and some of PGP's downsides are subtle.
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[liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread carlo von lynX
We had some debate on this topic at the Circumvention Tech
Summit and I got some requests to publish my six reasons
not to use PGP. Well, I spent a bit more time on it and now
they turned into 10 reasons not to. Some may appear similar
or identical, but actually they are on top of each other.
Corrections and religious flame wars are welcome. YMMV.



--
TEN REASONS NOT TO START USING PGP
--
   Coloured version at http://secushare.org/PGP



   [01]Pretty Good Privacy is better than no encryption at all, and being
   [02]end-to-end it is also better than relying on [03]SMTP over [04]TLS
   (that is, point-to-point between the mail servers while the message is
   unencrypted in-between), but is it still a good choice for the future?
   Is it something we should recommend to people who are asking for better
   privacy today?

1. Downgrade Attack: The risk of using it wrong.

   Modern cryptographic communication tools simply do not provide means to
   exchange messages without encryption. With e-mail the risk always
   remains that somebody will send you sensitive information in cleartext
   - simply because they can, because it is easier, because they don't
   have your public key yet and don't bother to find out about it, or just
   by mistake. Maybe even because they know they can make you angry that
   way - and excuse themselves pretending incompetence. Some people even
   manage to reply unencrypted to an encrypted message, although PGP
   software should keep them from doing so.

   The way you can simply not use encryption is also the number one
   problem with [05]OTR, the off-the-record cryptography method for
   instant messaging.

2. The OpenPGP Format: You might aswell run around the city naked.

   As Stf pointed out at CTS, thanks to its easily detectable [06]OpenPGP
   Message Format it is an easy exercise for any manufacturer of [07]Deep
   Packet Inspection hardware to offer a detection capability for
   PGP-encrypted messages anywhere in the flow of Internet communications,
   not only within SMTP. So by using PGP you are making yourself visible.

   Stf has been suggesting to use a non-detectable wrapping format. That's
   something, but it doesn't handle all the other problems with PGP.

3. Transaction Data: He knows who you are talking to.

   Should Mallory not [08]possess the private keys to your mail provider's
   TLS connection yet, he can simply intercept the communication by means
   of a [11]man-in-the-middle attack, using a valid fake certificate that
   he can make for himself on the fly. It's a bull run, you know?

   Even if you employ PGP, Mallory can trace who you are talking to, when
   and how long. He can guess at what you are talking about, especially
   since some of you will put something meaningful in the unencrypted
   Subject header.

   Should Mallory have been distracted, he can still recover your mails by
   visiting your provider's server. Something to do with a PRISM, I heard.
   On top of that, TLS itself is being recklessly deployed without forward
   secrecy most of the time.

4. No Forward Secrecy: It makes sense to collect it all.

   As Eddie has told us, Mallory is keeping a complete collection of all
   PGP mails being sent over the Internet, just in case the necessary
   private keys may one day fall into his hands. This makes sense because
   PGP lacks [12]forward secrecy. The characteristic by which encryption
   keys are frequently refreshed, thus the private key matching the
   message is soon destroyed. Technically PGP is capable of refreshing
   subkeys, but it is so tedious, it is not being practiced - let alone
   being practiced the way it should be: at least daily.

5. Cryptogeddon: Time to upgrade cryptography itself?

   Mallory may also be awaiting the day when RSA cryptography will be
   cracked and all encrypted messages will be retroactively readable.
   Anyone who recorded as much PGP traffic as possible will one day gain
   strategic advantages out of that. According to Mr Alex Stamos that day
   may be closer than PGP advocates think as [13]RSA cryptography may soon
   be cracked.

   This might be true, or it may be counter-intelligence to scare people
   away from RSA into the arms of [14]elleptic curve cryptography (ECC). A
   motivation to do so would have been to get people to use the curves
   recommended by the NIST, as they were created using magic numbers
   chosen without explanation by the NSA. No surprise they are suspected
   [15]to be corrupted.

   With both of these developments in mind, the alert cryptography
   activist scene seems now to converge on [16]Curve25519, a variant of
   ECC whose parameters where elaborated mathematically (they are the
   smallest numbers that satisfy all mathematical criteria that were set
   forth).

   ECC also happens to be a faster and more compact encryption technique,
   which you should take 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jillian C. York
In my opinion, this makes about as much sense as telling people who are
already having sex not to use condoms.

Consider mine a critique of why this post makes almost no sense to and
won't convince any member of the public.  I'm sure some of the geeks here
will have a field day with it, but some of it is barely in my realm of
understanding (and while I'm admittedly not a 'geek', I've been working in
this field for a long time, which puts me at the top rung of your 'average
user' base).

TL;DR: This may well be a solid argument for convincing developers to
implement better UIs, etc, but it doesn't work for its intended purpose,
which seems to be convincing n00bs not to use PGP.

(Detailed snark in-line)


On Thu, Oct 10, 2013 at 12:23 PM, carlo von lynX 
l...@time.to.get.psyced.org wrote:

 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.



 --
 TEN REASONS NOT TO START USING PGP
 --
Coloured version at http://secushare.org/PGP



[01]Pretty Good Privacy is better than no encryption at all, and being
[02]end-to-end it is also better than relying on [03]SMTP over [04]TLS
(that is, point-to-point between the mail servers while the message is
unencrypted in-between), but is it still a good choice for the future?
Is it something we should recommend to people who are asking for better
privacy today?

 1. Downgrade Attack: The risk of using it wrong.

Modern cryptographic communication tools simply do not provide means to
exchange messages without encryption. With e-mail the risk always
remains that somebody will send you sensitive information in cleartext
- simply because they can, because it is easier, because they don't
have your public key yet and don't bother to find out about it, or just
by mistake. Maybe even because they know they can make you angry that
way - and excuse themselves pretending incompetence. Some people even
manage to reply unencrypted to an encrypted message, although PGP
software should keep them from doing so.

The way you can simply not use encryption is also the number one
problem with [05]OTR, the off-the-record cryptography method for
instant messaging.


Okay, I'm not going to argue that PGP isn't hard or that people don't use
it incorrectly at times.  But would you say don't use condoms because
they're ineffective sometimes?  No, you would not.

This is a reason to improve the UI of PGP/OTR for sure, but not a reason
not to use it.



 2. The OpenPGP Format: You might aswell run around the city naked.

As Stf pointed out at CTS, thanks to its easily detectable [06]OpenPGP
Message Format it is an easy exercise for any manufacturer of [07]Deep
Packet Inspection hardware to offer a detection capability for
PGP-encrypted messages anywhere in the flow of Internet communications,
not only within SMTP. So by using PGP you are making yourself visible.

Stf has been suggesting to use a non-detectable wrapping format. That's
something, but it doesn't handle all the other problems with PGP.


Okay, this part requires more explanation for the layman, methinks.  It's
not intuitive for a non-tech to understand.



 3. Transaction Data: He knows who you are talking to.

Should Mallory not [08]possess the private keys to your mail provider's
TLS connection yet, he can simply intercept the communication by means
of a [11]man-in-the-middle attack, using a valid fake certificate that
he can make for himself on the fly. It's a bull run, you know?


You're not going to convince anyone with jargony talk.


Even if you employ PGP, Mallory can trace who you are talking to, when
and how long. He can guess at what you are talking about, especially
since some of you will put something meaningful in the unencrypted
Subject header.


Again, this is a call for better education around email practices, not for
people to stop using PGP.


Should Mallory have been distracted, he can still recover your mails by
visiting your provider's server. Something to do with a PRISM, I heard.
On top of that, TLS itself is being recklessly deployed without forward
secrecy most of the time.

 4. No Forward Secrecy: It makes sense to collect it all.

As Eddie has told us, Mallory is keeping a complete collection of all
PGP mails being sent over the Internet, just in case the necessary
private keys may one day fall into his hands. This makes sense because
PGP lacks [12]forward secrecy. The characteristic by which encryption
keys are frequently refreshed, thus the private 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jason Gulledge
Also, the premise of your argument, 10 reasons not to start, presupposes the 
truth of your argument, essentially begigng the question. Not that it makes 
your other arguments invalid, but I cringed when I saw the title, and also 
laughed. 

- Jason Gulledge


On Oct 10, 2013, at 9:40 PM, Jillian C. York jilliancy...@gmail.com wrote:

 In my opinion, this makes about as much sense as telling people who are 
 already having sex not to use condoms. 
 
 Consider mine a critique of why this post makes almost no sense to and won't 
 convince any member of the public.  I'm sure some of the geeks here will have 
 a field day with it, but some of it is barely in my realm of understanding 
 (and while I'm admittedly not a 'geek', I've been working in this field for a 
 long time, which puts me at the top rung of your 'average user' base).
 
 TL;DR: This may well be a solid argument for convincing developers to 
 implement better UIs, etc, but it doesn't work for its intended purpose, 
 which seems to be convincing n00bs not to use PGP.
 
 (Detailed snark in-line)
 
 
 On Thu, Oct 10, 2013 at 12:23 PM, carlo von lynX 
 l...@time.to.get.psyced.org wrote:
 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.
 
 
 
 --
 TEN REASONS NOT TO START USING PGP
 --
Coloured version at http://secushare.org/PGP
 
 
 
[01]Pretty Good Privacy is better than no encryption at all, and being
[02]end-to-end it is also better than relying on [03]SMTP over [04]TLS
(that is, point-to-point between the mail servers while the message is
unencrypted in-between), but is it still a good choice for the future?
Is it something we should recommend to people who are asking for better
privacy today?
 
 1. Downgrade Attack: The risk of using it wrong.
 
Modern cryptographic communication tools simply do not provide means to
exchange messages without encryption. With e-mail the risk always
remains that somebody will send you sensitive information in cleartext
- simply because they can, because it is easier, because they don't
have your public key yet and don't bother to find out about it, or just
by mistake. Maybe even because they know they can make you angry that
way - and excuse themselves pretending incompetence. Some people even
manage to reply unencrypted to an encrypted message, although PGP
software should keep them from doing so.
 
The way you can simply not use encryption is also the number one
problem with [05]OTR, the off-the-record cryptography method for
instant messaging.
 
 Okay, I'm not going to argue that PGP isn't hard or that people don't use it 
 incorrectly at times.  But would you say don't use condoms because they're 
 ineffective sometimes?  No, you would not.
 
 This is a reason to improve the UI of PGP/OTR for sure, but not a reason not 
 to use it.
  
 
 2. The OpenPGP Format: You might aswell run around the city naked.
 
As Stf pointed out at CTS, thanks to its easily detectable [06]OpenPGP
Message Format it is an easy exercise for any manufacturer of [07]Deep
Packet Inspection hardware to offer a detection capability for
PGP-encrypted messages anywhere in the flow of Internet communications,
not only within SMTP. So by using PGP you are making yourself visible.
 
Stf has been suggesting to use a non-detectable wrapping format. That's
something, but it doesn't handle all the other problems with PGP.
 
 Okay, this part requires more explanation for the layman, methinks.  It's not 
 intuitive for a non-tech to understand.
  
 
 3. Transaction Data: He knows who you are talking to.
 
Should Mallory not [08]possess the private keys to your mail provider's
TLS connection yet, he can simply intercept the communication by means
of a [11]man-in-the-middle attack, using a valid fake certificate that
he can make for himself on the fly. It's a bull run, you know?
 
 You're not going to convince anyone with jargony talk. 
 
Even if you employ PGP, Mallory can trace who you are talking to, when
and how long. He can guess at what you are talking about, especially
since some of you will put something meaningful in the unencrypted
Subject header.
 
 Again, this is a call for better education around email practices, not for 
 people to stop using PGP. 
 
Should Mallory have been distracted, he can still recover your mails by
visiting your provider's server. Something to do with a PRISM, I heard.
On top of that, TLS itself is being recklessly deployed without forward
secrecy most of the time.
 
 4. No 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Griffin Boyce
  While there are easy ways to mess up using PGP, I think that a more
well-rounded approach is to be mindful of the ways that one can be
de-anonymized (by others or themselves) while using it.

  People who don't have a holistic view of their security, and don't
want to learn more about their actual threats and risks/rewards of
encryption won't be well-served by PGP or OTR or full-disk encryption.

  Without informed consent, encryption is meaningless.  That is not to
say that encryption is always meaningless.

~Griffin


On 10/10/2013 03:23 PM, carlo von lynX wrote:
 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.



   --
   TEN REASONS NOT TO START USING PGP
   --
Coloured version at http://secushare.org/PGP

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

My posts are my own, not my employer's.

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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread adrelanos
Thank you for doing this work!

The world needs someone facing the truth, explaining why gpg isn't the
solution, advocating positive change. It's a communicative task, a very
difficult one. As long there is gpg, most geeks don't see need to create
better alternatives.

I'd say, gpg's development slowed down. They're qualified but standing
in their own way. They should break compatibility with commercial PGP
(not because thats good, just because it's easier to implement better
solutions), also break compatibility with RFCs, implement better
solutions and standardize later. The current first standardize, then
maybe implement, and don't implement if it's not standardized approach
is much too slow, can't keep up with real developments in real word.
(Still don't even have mail subject encryption.) If Bitmessage succeeds
(I haven't learned much about it yet), and actually provides better
protection than gpg, I am happy with that also if there isn't a RFC. If
Bitmessage gets really popular, I am sure they'll somehow work things
out and happen to standardize it later.

Sometimes I even think, if there wasn't gpg, new approaches had better
chances reaching critical mass.

carlo von lynX:
 But what should I do then!??
 
So that now we know 10 reasons not to use PGP over e-mail, let's first
acknowledge that there is no easy answer. Electronic privacy is a crime
zone with blood freshly spilled all over. None of the existing tools
are fully good enough.

I am a gpg user myself, but must say that it has really awful usability.
OTR has so much better usability, but it it (yet?) can't be used to sign
files or for higher latency communication (e-mail).

I agree, the existing tools aren't remotely good enough.

 Thank you, PGP.

Thanks for acknowledging that.
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Richard Brooks
10 reasons to give up, stop trying, hide in a corner, and die.

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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Pranesh Prakash
Interesting. But someone should also write a piece called 1 reason not
to criticise security tech without clearly stating threat model which
serves as basis for that criticism.  What if Mallory isn't a
well-funded governmental organization but is the admin who runs your
employer's email servers?

This should actually be two lists: reasons not to use e-mail, and
reasons not to use OpenPGP over e-mail.

Only reasons 2, 3, 4, 5, 7, 8 are really about OpenPGP (you should've
stuck to 6 reasons not to use PGP), and at least three of them are
really good reasons to look for alternatives. There are no good
alternatives over e-mail: S/MIME unfortunately suffers from many of the
same issues as OpenPGP, and then some more.

And reason #1 is something that the client should take care of (ideally
with default settings), and not the encryption protocol.  Why are you
attacking OpenPGP and OTR for this?

And thank you so much for the comparative chart.  It is *very* useful.

Why doesn't telephony have SIP?

~ Pranesh

carlo von lynX [2013-10-10 15:23]:
 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.
 
 
 
   --
   TEN REASONS NOT TO START USING PGP
   --
Coloured version at http://secushare.org/PGP
 
 
 
[01]Pretty Good Privacy is better than no encryption at all, and being
[02]end-to-end it is also better than relying on [03]SMTP over [04]TLS
(that is, point-to-point between the mail servers while the message is
unencrypted in-between), but is it still a good choice for the future?
Is it something we should recommend to people who are asking for better
privacy today?
 
 1. Downgrade Attack: The risk of using it wrong.
 
Modern cryptographic communication tools simply do not provide means to
exchange messages without encryption. With e-mail the risk always
remains that somebody will send you sensitive information in cleartext
- simply because they can, because it is easier, because they don't
have your public key yet and don't bother to find out about it, or just
by mistake. Maybe even because they know they can make you angry that
way - and excuse themselves pretending incompetence. Some people even
manage to reply unencrypted to an encrypted message, although PGP
software should keep them from doing so.
 
The way you can simply not use encryption is also the number one
problem with [05]OTR, the off-the-record cryptography method for
instant messaging.
 
 2. The OpenPGP Format: You might aswell run around the city naked.
 
As Stf pointed out at CTS, thanks to its easily detectable [06]OpenPGP
Message Format it is an easy exercise for any manufacturer of [07]Deep
Packet Inspection hardware to offer a detection capability for
PGP-encrypted messages anywhere in the flow of Internet communications,
not only within SMTP. So by using PGP you are making yourself visible.
 
Stf has been suggesting to use a non-detectable wrapping format. That's
something, but it doesn't handle all the other problems with PGP.
 
 3. Transaction Data: He knows who you are talking to.
 
Should Mallory not [08]possess the private keys to your mail provider's
TLS connection yet, he can simply intercept the communication by means
of a [11]man-in-the-middle attack, using a valid fake certificate that
he can make for himself on the fly. It's a bull run, you know?
 
Even if you employ PGP, Mallory can trace who you are talking to, when
and how long. He can guess at what you are talking about, especially
since some of you will put something meaningful in the unencrypted
Subject header.
 
Should Mallory have been distracted, he can still recover your mails by
visiting your provider's server. Something to do with a PRISM, I heard.
On top of that, TLS itself is being recklessly deployed without forward
secrecy most of the time.
 
 4. No Forward Secrecy: It makes sense to collect it all.
 
As Eddie has told us, Mallory is keeping a complete collection of all
PGP mails being sent over the Internet, just in case the necessary
private keys may one day fall into his hands. This makes sense because
PGP lacks [12]forward secrecy. The characteristic by which encryption
keys are frequently refreshed, thus the private key matching the
message is soon destroyed. Technically PGP is capable of refreshing
subkeys, but it is so tedious, it is not being practiced - let alone
being practiced the way it should be: at least daily.
 
 5. Cryptogeddon: Time to upgrade cryptography itself?
 
Mallory may also be 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Marcin de Kaminski
Agreed. The threat model discussion clearly is too often lost in all the 
current post-Snowden debates. We need to remember that a lot if solutions might 
not be enough to protect anyone against NSAish authorities but more than enough 
against other, most real, threats to peoples personal safety. Regular 
employers, schools, parents, skiddies, whatever. 

Marcin

 10 okt 2013 kl. 22:11 skrev Pranesh Prakash pran...@cis-india.org:
 
 Interesting. But someone should also write a piece called 1 reason not
 to criticise security tech without clearly stating threat model which
 serves as basis for that criticism.  What if Mallory isn't a
 well-funded governmental organization but is the admin who runs your
 employer's email servers?
 
 This should actually be two lists: reasons not to use e-mail, and
 reasons not to use OpenPGP over e-mail.
 
 Only reasons 2, 3, 4, 5, 7, 8 are really about OpenPGP (you should've
 stuck to 6 reasons not to use PGP), and at least three of them are
 really good reasons to look for alternatives. There are no good
 alternatives over e-mail: S/MIME unfortunately suffers from many of the
 same issues as OpenPGP, and then some more.
 
 And reason #1 is something that the client should take care of (ideally
 with default settings), and not the encryption protocol.  Why are you
 attacking OpenPGP and OTR for this?
 
 And thank you so much for the comparative chart.  It is *very* useful.
 
 Why doesn't telephony have SIP?
 
 ~ Pranesh
 
 carlo von lynX [2013-10-10 15:23]:
 We had some debate on this topic at the Circumvention Tech
 Summit and I got some requests to publish my six reasons
 not to use PGP. Well, I spent a bit more time on it and now
 they turned into 10 reasons not to. Some may appear similar
 or identical, but actually they are on top of each other.
 Corrections and religious flame wars are welcome. YMMV.
 
 
 
--
TEN REASONS NOT TO START USING PGP
--
   Coloured version at http://secushare.org/PGP
 
 
 
   [01]Pretty Good Privacy is better than no encryption at all, and being
   [02]end-to-end it is also better than relying on [03]SMTP over [04]TLS
   (that is, point-to-point between the mail servers while the message is
   unencrypted in-between), but is it still a good choice for the future?
   Is it something we should recommend to people who are asking for better
   privacy today?
 
 1. Downgrade Attack: The risk of using it wrong.
 
   Modern cryptographic communication tools simply do not provide means to
   exchange messages without encryption. With e-mail the risk always
   remains that somebody will send you sensitive information in cleartext
   - simply because they can, because it is easier, because they don't
   have your public key yet and don't bother to find out about it, or just
   by mistake. Maybe even because they know they can make you angry that
   way - and excuse themselves pretending incompetence. Some people even
   manage to reply unencrypted to an encrypted message, although PGP
   software should keep them from doing so.
 
   The way you can simply not use encryption is also the number one
   problem with [05]OTR, the off-the-record cryptography method for
   instant messaging.
 
 2. The OpenPGP Format: You might aswell run around the city naked.
 
   As Stf pointed out at CTS, thanks to its easily detectable [06]OpenPGP
   Message Format it is an easy exercise for any manufacturer of [07]Deep
   Packet Inspection hardware to offer a detection capability for
   PGP-encrypted messages anywhere in the flow of Internet communications,
   not only within SMTP. So by using PGP you are making yourself visible.
 
   Stf has been suggesting to use a non-detectable wrapping format. That's
   something, but it doesn't handle all the other problems with PGP.
 
 3. Transaction Data: He knows who you are talking to.
 
   Should Mallory not [08]possess the private keys to your mail provider's
   TLS connection yet, he can simply intercept the communication by means
   of a [11]man-in-the-middle attack, using a valid fake certificate that
   he can make for himself on the fly. It's a bull run, you know?
 
   Even if you employ PGP, Mallory can trace who you are talking to, when
   and how long. He can guess at what you are talking about, especially
   since some of you will put something meaningful in the unencrypted
   Subject header.
 
   Should Mallory have been distracted, he can still recover your mails by
   visiting your provider's server. Something to do with a PRISM, I heard.
   On top of that, TLS itself is being recklessly deployed without forward
   secrecy most of the time.
 
 4. No Forward Secrecy: It makes sense to collect it all.
 
   As Eddie has told us, Mallory is keeping a complete collection of all
   PGP mails being sent over the Internet, just in case the necessary
   private keys may one day fall into his hands. This makes sense because
   PGP lacks 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jonathan Wilkes

On 10/10/2013 03:55 PM, adrelanos wrote:

Thank you for doing this work!

The world needs someone facing the truth, explaining why gpg isn't the
solution, advocating positive change. It's a communicative task, a very
difficult one. As long there is gpg, most geeks don't see need to create
better alternatives.

I'd say, gpg's development slowed down. They're qualified but standing
in their own way. They should break compatibility with commercial PGP
(not because thats good, just because it's easier to implement better
solutions), also break compatibility with RFCs, implement better
solutions and standardize later. The current first standardize, then
maybe implement, and don't implement if it's not standardized approach
is much too slow, can't keep up with real developments in real word.
(Still don't even have mail subject encryption.) If Bitmessage succeeds
(I haven't learned much about it yet),


Bitmessage doesn't have forward secrecy, and AFAICT there's no
way to easily add it later on.

Best,
Jonathan
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jillian C. York
+1 - you said it much better than me.


On Thu, Oct 10, 2013 at 1:55 PM, Enrique Piracés enriq...@benetech.orgwrote:

 -BEGIN PGP SIGNED MESSAGE-
 Hash: SHA512

 Hi there,

 I think this is a good topic for debate among those who can or are
 currently developing security tools/protocols, and it is one way to
 further discuss usability as a security feature in communities like
 this one. That said, I think it is really bad advice and I encourage
 you to refrain from providing this as a suggestion for users who may
 put themselves or others at risk as a result of it.

 Also, I think the title is misleading, as most of the article is about
 why PGP is not an ideal solution for the future (a point where I think
 you would find significant agreement). Again, suggesting not to use
 PGP without providing a functional alternative is irresponsible.

 Best,
 Enrique
 - --
 Enrique Piracés
 Vice President, Human Rights Program
 Benetech

 https://www.benetech.org
 https://www.martus.org
 https://www.twitter.com/epiraces

 On 10/10/13 3:23 PM, carlo von lynX wrote:
  We had some debate on this topic at the Circumvention Tech Summit
  and I got some requests to publish my six reasons not to use PGP.
  Well, I spent a bit more time on it and now they turned into 10
  reasons not to. Some may appear similar or identical, but actually
  they are on top of each other. Corrections and religious flame wars
  are welcome. YMMV.
 
 
 
  -- TEN REASONS NOT TO START USING
  PGP -- Coloured version at
  http://secushare.org/PGP
 
 
 
  [01]Pretty Good Privacy is better than no encryption at all, and
  being [02]end-to-end it is also better than relying on [03]SMTP
  over [04]TLS (that is, point-to-point between the mail servers
  while the message is unencrypted in-between), but is it still a
  good choice for the future? Is it something we should recommend to
  people who are asking for better privacy today?
 
  1. Downgrade Attack: The risk of using it wrong.
 
  Modern cryptographic communication tools simply do not provide
  means to exchange messages without encryption. With e-mail the risk
  always remains that somebody will send you sensitive information in
  cleartext - simply because they can, because it is easier, because
  they don't have your public key yet and don't bother to find out
  about it, or just by mistake. Maybe even because they know they can
  make you angry that way - and excuse themselves pretending
  incompetence. Some people even manage to reply unencrypted to an
  encrypted message, although PGP software should keep them from
  doing so.
 
  The way you can simply not use encryption is also the number one
  problem with [05]OTR, the off-the-record cryptography method for
  instant messaging.
 
  2. The OpenPGP Format: You might aswell run around the city naked.
 
  As Stf pointed out at CTS, thanks to its easily detectable
  [06]OpenPGP Message Format it is an easy exercise for any
  manufacturer of [07]Deep Packet Inspection hardware to offer a
  detection capability for PGP-encrypted messages anywhere in the
  flow of Internet communications, not only within SMTP. So by using
  PGP you are making yourself visible.
 
  Stf has been suggesting to use a non-detectable wrapping format.
  That's something, but it doesn't handle all the other problems with
  PGP.
 
  3. Transaction Data: He knows who you are talking to.
 
  Should Mallory not [08]possess the private keys to your mail
  provider's TLS connection yet, he can simply intercept the
  communication by means of a [11]man-in-the-middle attack, using a
  valid fake certificate that he can make for himself on the fly.
  It's a bull run, you know?
 
  Even if you employ PGP, Mallory can trace who you are talking to,
  when and how long. He can guess at what you are talking about,
  especially since some of you will put something meaningful in the
  unencrypted Subject header.
 
  Should Mallory have been distracted, he can still recover your
  mails by visiting your provider's server. Something to do with a
  PRISM, I heard. On top of that, TLS itself is being recklessly
  deployed without forward secrecy most of the time.
 
  4. No Forward Secrecy: It makes sense to collect it all.
 
  As Eddie has told us, Mallory is keeping a complete collection of
  all PGP mails being sent over the Internet, just in case the
  necessary private keys may one day fall into his hands. This makes
  sense because PGP lacks [12]forward secrecy. The characteristic by
  which encryption keys are frequently refreshed, thus the private
  key matching the message is soon destroyed. Technically PGP is
  capable of refreshing subkeys, but it is so tedious, it is not
  being practiced - let alone being practiced the way it should be:
  at least daily.
 
  5. Cryptogeddon: Time to upgrade cryptography itself?
 
  Mallory may also be awaiting the day when RSA cryptography will be
  cracked and all 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Gregory Maxwell
I'm surprised to see this list has missed the thing that bugs me most
about PGP: It conflates non-repudiation and authentication.

I send Bob an encrypted message that we should meet to discuss the
suppression of free speech in our country. Bob obviously wants to be
sure that the message is coming from me, but maybe Bob is a spy ...
and with PGP the only way the message can easily be authenticated as
being from me is if I cryptographically sign the message, creating
persistent evidence of my words not just to Bob but to Everyone!

When there are only two parties in an encrypted communication this is
_trivial_ to solve cryptographically: just use DH to compute a shared
secret and use it to authenticate the message.  (Multiple parties is
solvable too, but requires a ring signature or other more complicated
solution).

But PGP has no real solutions for that.

My other big technical complaint about PGP is (3) in the post, that
every encrypted message discloses what key you're communicating with.
PGP easily _undoes_ the privacy that an anonymity network like tor can
provide.  It's possible to use --hidden-recipient but almost no one
does.

Its also easy to produce a litany of non-technical complaints: PGP is
almost universally misused (even by people whos lives may depend on
its correct use), the WOT leaks tons of data, etc.

In my view the use of PGP is more appropriately seen as a statement
about the kind of world we want to have— one where encryption is
lawful, widely used, and uncontroversial— and less of a practical way
to achieve security against many threats that exist today.
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread elijah
On 10/10/2013 12:23 PM, carlo von lynX wrote:

 1. Downgrade Attack: The risk of using it wrong.

Fixed in the new generation of clients (mailpile, LEAP, etc).

 2. The OpenPGP Format: You might aswell run around the city naked.

Fixed by using StartTLS with DANE (supported in the new version of
postfix). Admittedly, this makes sysadmin's job more challenging, but
LEAP is working to automate the hard stuff (https://leap.se/platform).

 3. Transaction Data: He knows who you are talking to.

Fixed in the short term by using StartTLS with DANE. Fixed in the long
term by adopting one of these approaches: https://leap.se/en/routing

 4. No Forward Secrecy: It makes sense to collect it all.

Imperfectly fixed in the short term using StartTLS with only PFS ciphers
enabled. This could be fixed in the long term by using Trevor Perrin's
scheme for triple EC Diffie-Hellman exchange. This has been implemented
by moxie for SMS, and could be for SMTP
(https://whispersystems.org/blog/simplifying-otr-deniability/).

 5. Cryptogeddon: Time to upgrade cryptography itself?

New version of GPG supports ECC, but of course nothing in the snowden
leaks suggest we need to abandon RSA of sufficient key length (just the
ECC curves that have *always* been suspicious).

 6. Federation: Get off the inter-server super-highway.

Federated transport with spool-then-forward time delay is likely a much
more feasible way to thwart traffic analysis than attempting to lay down
a high degree of cover traffic for direct peer to peer transport. This
is, of course, an area of active academic research and it would be
irresponsible to say that we definitively know how to prevent traffic
analysis, either with p2p or federation.

 7. Statistical Analysis: Guessing on the size of messages.

Easily fixed.

 8. Workflow: Group messaging with PGP is impractical.

No one anywhere has solved the problem of asynchronous, forward-secret
group cryptography. There are, however, working models of group
cryptography using OpenPGP, such as SELS
(http://sels.ncsa.illinois.edu/). This approach makes key management
more difficult, but we need to automate key management anyway for
OpenPGP to be usable enough for wider adoption.

 9. TL;DR: I don't care. I've got nothing to hide.

This critique rests on the assumption that the problems with email are
unfixable.

 10. The Bootstrap Fallacy: But my friends already have e-mail!

Email remains one of the two killer apps of the internet, and is
unlikely to vanish any time soon. Simple steps we can take to make it
much better seem like a wise investment in energy.

There are two approaches to addressing the problems with email:

(1) assert that email is hopeless and must be killed off.
(2) identify areas where we can fix email to bring it into the 21st century.

I think that approach #1 is irresponsible: regardless of one's personal
feelings about email, it is certainly not a lost cause, and asserting
that it is will make it more difficult to build support for fixing it.

Approach #2 is certainly an uphill battle, but there are a growing
number of organizations working on it. LEAP's (free software) efforts
are outlined here: https://leap.se/email. We have it working, we just
need to get it mature enough for production use.

-elijah
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread carlo von lynX
Hello again. I will answer to most comments all in a single mail
to avoid clogging libtech. While I wrote this another ten mails
have slipped in, so expect another large reply to those.  :-)


On 10/10/2013 10:00 PM, Richard Brooks wrote:
 10 reasons to give up, stop trying, hide in a corner, and die.

Sorry if I start talking about the alternatives only at the very end
of the document. This is about becoming aware of how serious the
problem is and to start directing some energy into fueling the
alternatives which are popping up like mushrooms just recently.
For the obvious reasons. And I specifically mention peer reviewing
them. So the message is: go get yourself new tools and teach your
peers to use the new tool of the day.


On 10/10/2013 10:11 PM, Pranesh Prakash wrote:
 Interesting. But someone should also write a piece called 1 reason not
 to criticise security tech without clearly stating threat model which
 serves as basis for that criticism.  What if Mallory isn't a
 well-funded governmental organization but is the admin who runs your
 employer's email servers?

That's a good point. The reason why I don't pay attention to lesser
threat models is that the loss in quality of democracy we are currently
experiencing is large enough that I don't see much use for a distinction
of threat models - especially since alternatives that work better than
PGP exist, so they are obviously also better for lesser threat models.

For example, I don't think that a dissident in Irya (ficticious country)
is better off if no-one but Google Mail knows that he is a dissident.
Should at any later time in his life someone with access to that data
find it useful to use it against the dissident, he can still do it.
And who knows what the world looks like in twenty years from now?

Not saying give up and die. Saying if you can opt for better security,
don't postpone learning about it. If you can invest money in making
it a safe option, don't waste time with yet another PGP GUI project.

 This should actually be two lists: reasons not to use e-mail, and
 reasons not to use OpenPGP over e-mail.

Fine with me. I don't think it makes much difference for the end
user whether SMTP federation or actual PGP is failing her.

 Only reasons 2, 3, 4, 5, 7, 8 are really about OpenPGP (you should've
 stuck to 6 reasons not to use PGP), and at least three of them are
 really good reasons to look for alternatives. There are no good
 alternatives over e-mail: S/MIME unfortunately suffers from many of the
 same issues as OpenPGP, and then some more.

I don't find S/MIME worth mentioning anymore. It has so failed us.
But maybe I should for completeness?

 And reason #1 is something that the client should take care of (ideally
 with default settings), and not the encryption protocol.  Why are you
 attacking OpenPGP and OTR for this?

Because it's not true that the client can handle it. The fact that an
email address exists implies that some folks will send unencrypted
stuff to it. I experienced this. Just yesterday a friend changed his
life plans because of an unencrypted message. Yes, you could enforce
PGP once it's configured - but you can't opt out from e-mail. That is
evil.

Look at any of the alternatives instead. None of them allow you to
transmit an unencrypted message. In fact all the modern systems use
the public key for addressing, so you can't do it wrong.

 And thank you so much for the comparative chart.  It is *very* useful.

My pleasure. I felt the need to do this since I get asked for
recommendations frequently - and I don't like to say.. wait until
secushare is ready. I don't want to wait for it myself.

 Why doesn't telephony have SIP?

It should. What would the icons be that you would put there?
I'm not familiar with end-to-end encryption over SIP for instance.


On 10/10/2013 10:33 PM, Marcin de Kaminski wrote:
 Agreed. The threat model discussion clearly is too often lost in all
 the current post-Snowden debates. We need to remember that a lot if
 solutions might not be enough to protect anyone against NSAish
 authorities but more than enough against other, most real, threats
 to peoples personal safety. Regular employers, schools, parents, skiddies, 
 whatever. 

I think if employers, schools, parents, skiddies can find out who
you are exchanging encrypted messages with, that can be a very real
threat to you. Using a tool that looks like it does something
totally different.. on your screen, over the network and even on
your hard disk.. can save your physical integrity.


On 10/10/2013 09:55 PM, adrelanos wrote:
 Thank you for doing this work!
 The world needs someone facing the truth, explaining why gpg isn't the
 solution, advocating positive change. It's a communicative task, a very
 difficult one. As long there is gpg, most geeks don't see need to create
 better alternatives.

Glad someone is understanding the positivity in awareness and
will to move forward. Ignoring threats just because they are
depressing is a bit 

Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jillian C. York
Just replying to this bit of your reply to me; the rest made sense

On Thu, Oct 10, 2013 at 3:08 PM, carlo von lynX l...@time.to.get.psyced.org
 wrote:

 If this is still jargony to you, hmmm... you are unlikely to understand
 the risks you are exposed to by using the Internet from day to day.
 These are concepts that anyone in the circumvention business must
 be aware of. You can choose to not read the Guardian article and not
 try to understand what's going on, but then you should better just
 trust that the conclusion is not made up:


No, see that's the thing: *I *get it, but I don't think I'm totally your
target audience (I've been using PGP for years, you're talking to people
who haven't started yet, right?)

You want criticism?  There it is.  Your writing does not work for the
general public.  You write in a way that feels condescending and assumes
that the reader already has a full grasp of why those things are issues.
 On the one hand, you're telling people that PGP is too hard/broken, while
with the other you're expecting them to already understand it/the threat
model.

Also, I have no idea what is meant by the bull run comment in that
sentence. If you want your piece to have any reach beyond the English
language, consider tightening up your writing.



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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread Jillian C. York
Ah, I see you probably meant BULLRUN. Guess it just wasn't a well-executed
pun.


On Thu, Oct 10, 2013 at 3:17 PM, Jillian C. York jilliancy...@gmail.comwrote:


 Just replying to this bit of your reply to me; the rest made sense

 On Thu, Oct 10, 2013 at 3:08 PM, carlo von lynX 
 l...@time.to.get.psyced.org wrote:

 If this is still jargony to you, hmmm... you are unlikely to understand
 the risks you are exposed to by using the Internet from day to day.
 These are concepts that anyone in the circumvention business must
 be aware of. You can choose to not read the Guardian article and not
 try to understand what's going on, but then you should better just
 trust that the conclusion is not made up:


 No, see that's the thing: *I *get it, but I don't think I'm totally your
 target audience (I've been using PGP for years, you're talking to people
 who haven't started yet, right?)

 You want criticism?  There it is.  Your writing does not work for the
 general public.  You write in a way that feels condescending and assumes
 that the reader already has a full grasp of why those things are issues.
  On the one hand, you're telling people that PGP is too hard/broken, while
 with the other you're expecting them to already understand it/the threat
 model.

 Also, I have no idea what is meant by the bull run comment in that
 sentence. If you want your piece to have any reach beyond the English
 language, consider tightening up your writing.




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*Note: *I am slowly extricating myself from Gmail. Please change your
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seemingly impossible to become a reality - *Vaclav Havel*
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Re: [liberationtech] 10 reasons not to start using PGP

2013-10-10 Thread carlo von lynX
Next collection of answers to replies.
Expect yours to be somewhere in here.
Thanks for all the feedback!
I actually expected harsher religious replies!  :)


On 10/10/2013 10:55 PM, Enrique Piracés wrote:
 I think this is a good topic for debate among those who can or are
 currently developing security tools/protocols, and it is one way to
 further discuss usability as a security feature in communities like
 this one. That said, I think it is really bad advice and I encourage
 you to refrain from providing this as a suggestion for users who may
 put themselves or others at risk as a result of it.

The opening sentence says
Pretty Good Privacy is better than no encryption at all ...

 Also, I think the title is misleading, as most of the article is about
 why PGP is not an ideal solution for the future (a point where I think
 you would find significant agreement). Again, suggesting not to use
 PGP without providing a functional alternative is irresponsible.

I am suggesting four alternatives and indicating to work harder
to make them viable tools for everyone as we should no longer postpone
replacing PGP and e-mail. Of course I would also appreciate attention
regarding the fifth, secushare.


On 10/10/2013 10:57 PM, Jonathan Wilkes wrote:
 Bitmessage doesn't have forward secrecy, and AFAICT there's no
 way to easily add it later on.

If I understood the principle correctly it allows you to generate
new accounts freely, so you can put your *next* account name into
a message. If both sides do this, they can obfuscate their identities
a bit. And you can automate it. You could also re-key at each
message with PGP, but I presume it would make your implementation
incompatible with everybody else's.


On 10/10/2013 11:08 PM, Gregory Maxwell wrote:
 I'm surprised to see this list has missed the thing that bugs me most
 about PGP: It conflates non-repudiation and authentication.
 
 I send Bob an encrypted message that we should meet to discuss the
 suppression of free speech in our country. Bob obviously wants to be
 sure that the message is coming from me, but maybe Bob is a spy ...
 and with PGP the only way the message can easily be authenticated as
 being from me is if I cryptographically sign the message, creating
 persistent evidence of my words not just to Bob but to Everyone!

I kind-of lumped it mentally together with forward secrecy, because
for both problems the answer is Diffie-Hellman. But you are right, it
is the eleventh reason.

 My other big technical complaint about PGP is (3) in the post, that
 every encrypted message discloses what key you're communicating with.
 PGP easily _undoes_ the privacy that an anonymity network like tor can
 provide.  It's possible to use --hidden-recipient but almost no one
 does.

Guess what, none of the alternative messaging tools would dream of
putting the recipient address close to the message. They just make
sure that it somehow gets there.

 Its also easy to produce a litany of non-technical complaints: PGP is
 almost universally misused (even by people whos lives may depend on
 its correct use), the WOT leaks tons of data, etc.

Oh yes, I completely forgot to link that long article that recently
came out criticizing the PGP web of trust.

 In my view the use of PGP is more appropriately seen as a statement
 about the kind of world we want to have— one where encryption is
 lawful, widely used, and uncontroversial— and less of a practical way
 to achieve security against many threats that exist today.

It is not enough for the purpose of protecting democracy, therefore
it's one of those statements that backfire: The adversary doesn't
care about you making that statement and can use it against you.


On 10/11/2013 12:17 AM, Jillian C. York wrote:
 Just replying to this bit of your reply to me; the rest made sense

Grrreat.

 On Thu, Oct 10, 2013 at 3:08 PM, carlo von lynX
 l...@time.to.get.psyced.org mailto:l...@time.to.get.psyced.org wrote:
 
If this is still jargony to you, hmmm... you are unlikely to understand
the risks you are exposed to by using the Internet from day to day.
These are concepts that anyone in the circumvention business must
be aware of. You can choose to not read the Guardian article and not
try to understand what's going on, but then you should better just
trust that the conclusion is not made up:
 
 No, see that's the thing: /I /get it, but I don't think I'm totally your
 target audience (I've been using PGP for years, you're talking to people
 who haven't started yet, right?)

No, not really. It is for the multipliers and activists. The ones that
carry the torch to the people. The Luciphers. You have been carrying
PGP to the people and I am suggesting you should consider giving them
other tools, and educating them to question those tools and look out
for even newer tools. And help make these tools safe, reviewed and usable.
Then again I wouldn't mind if normal people /get/ it, too, but I wouldn't
want them