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 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.
> 
> Again: Fair criticism, but unclear why this should convince one NOT to use 
> PGP.  Rather, it should convince us to improve mechanisms and add forward 
> secrecy. 
> 
> 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 as an incentive to increase the size of your
>    encryption keys. It is up to you to worry if it's more likely that RSA
>    or ECC will be cracked in future, or you may want to ask a
>    mathematician.
> 
> 6. Federation: Get off the inter-server super-highway.
> 
>    NSA officials have been reported saying that NSA does not keep track of
>    all the peer-to-peer traffic as it is just large amounts of mostly
>    irrelevant copyright infringement. It is thus a very good idea to
>    develop a communications tool that embeds its ECC- encrypted
>    information into plenty of P2P cover traffic.
> 
>    Although this information is only given by hearsay, it is a reasonable
>    consideration to make. By travelling the well-established and
>    surveilled paths of e-mail, PGP is unnecessarily superexposed. Would be
>    much better, if the same PGP was being handed from computer to computer
>    directly. Maybe even embedded into a picture, movie or piece of music
>    using [17]steganography.
> 
> Steganography, really?  Sigh.
>  
> 
> 7. Statistical Analysis: Guessing on the size of messages.
> 
>    Especially for chats and remote computer administration it is known
>    that the size and frequency of small encrypted snippets can be observed
>    long enough to guess the contents. This is a problem with SSH and OTR
>    more than with PGP, but also PGP would be smarter if the messages were
>    padded to certain standard sizes, making them look all uniform.
> 
> It would be great, yes.  Still doesn't convince me that using PGP isn't 
> worthwhile. 
> 
> 8. Workflow: Group messaging with PGP is impractical.
> 
>    Have you tried making a mailing list with people sharing private
>    messages? It's a cumbersome configuration procedure and inefficient
>    since each copy is re-encrypted. You can alternatively all share the
>    same key, but that's a different cumbersome configuration procedure.
> 
>    Modern communication tools automate the generation and distribution of
>    group session keys so you don't need to worry. You just open up a
>    working group and invite the people to work with.
> 
> Okay, yes, you've got me here.  PGP sucks for group discussion, although I 
> fail to see why group discussion is an imperative.  But what, do you suggest, 
> is an immediate alternative?   Nothing?  Right, okay...still using PGP.
> 
> 9. TL;DR: I don't care. I've got nothing to hide.
> 
>    So you think PGP is enough for you since you aren't saying anything
>    reaaally confidential? Nobody actually cares how much you want to lie
>    yourself stating you have nothing to hide. If that was the case, why
>    don't you do it on the street, as John Lennon used to ask?
> 
>    It's not about you, it's about your civic duty not to be a member of a
>    predictable populace. If somebody is able to know all your preferences,
>    habits and political views, you are causing severe damage to democratic
>    society. That's why it is not enough that you are covering naughty
>    parts of yourself with a bit of PGP, if all the rest of it is still in
>    the nude. Start feeling guilty. Now.
> 
> Again: This is merely a reason to convince people to use encryption MORE 
> OFTEN (which EFF does and which I fully support). 
> 
> 10. The Bootstrap Fallacy: But my friends already have e-mail!
> 
>    But everyone I know already has e-mail, so it is much easier to teach
>    them to use PGP. Why would I want to teach them a new software!?
> 
>    That's a fallacy. Truth is, all people that want to start improving
>    their privacy have to install new software. Be it on top of
>    super-surveilled e-mail or safely independent from it. In any case you
>    will have to make a [18]safe exchange of the public keys, and e-mail
>    won't be very helpful at that. In fact you make it easy for Mallory to
>    connect your identity to your public key for all future times.
> 
>    If you really think your e-mail consumption set-up is so amazing and
>    you absolutely don't want to start all over with a completely different
>    kind of software, look out for upcoming tools that let you use mail
>    clients on top. Not the other way around.
> 
> I don't even get what you're saying here.  What, do you suggest, is the new 
> software to teach people if not PGP? 
> 
> 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. We have to get used to the fact that new tools
>    will come out twice a year.
> 
> Cop-out. "Don't use PGP but I can't suggest anything for you."  Silly. 
> 
>    Mallory has an interest in making us believe encryption isn't going to
>    work anyway - but internal data leaked by Mr Snowden shows that
>    encryption actually works. We should just care to use it the best way.
>    That means, not with PGP.
> 
> There is no one magic bullet you can learn about.
> 
>    You have to get used to learning new software frequently. You have to
>    teach the basics of encryption independently from any software,
>    especially from the one that does it wrong the most.
> 
>    In the [09]comparison we have listed a few currently existing
>    technologies, that provide a safer messaging experience than PGP. The
>    problem with those frequently is, that they haven't been peer reviewed.
>    You may want to invest time or money in having projects peer reviewed
>    for safety.
> 
>    Pond is currently among the most interesting projects for mail privacy,
>    hiding its padded undetectable crypto in the general noise of Tor. Tor
>    is a good place to hide private communication since the bulk of Tor
>    traffic seems to be anonymized transactions with Facebook and the like.
>    Even better source of cover traffic is file sharing, that's why
>    RetroShare and GNUnet both have solid file sharing functionality to let
>    you hide your communications in.
> 
>    Mallory will try to adapt and keep track of our communications as we
>    dive into cover traffic, but it will be a very hard challenge for him,
>    also because all of these technologies are working to switch to
>    Curve25519. Secushare intends to only support Curve25519 to impede
>    [10]downgrade attacks. Until the next best practice comes out. It's an
>    arms race. Time to lay down your old bayonet while Mallory is pointing
>    a nuclear missile at you.
> 
> Thank you, PGP.
> 
>    Thank you Mr Zimmermann for bringing encryption technology to the
>    simple people, back in 1991. It has been an invaluable tool for twenty
>    years, we will never forget. But it is overdue to move on.
> 
> References
> 
>   01. https://en.wikipedia.org/wiki/Pretty%20Good%20Privacy
>   02. http://secushare.org/end2end
>   03. https://en.wikipedia.org/wiki/SMTP
>   04. https://en.wikipedia.org/wiki/TLS
>   05. https://en.wikipedia.org/wiki/Off-the-Record_Messaging
>   06. http://tools.ietf.org/html/rfc4880
>   07. https://en.wikipedia.org/wiki/Deep_packet_inspection
>   08. 
> http://www.theguardian.com/world/2013/sep/05/nsa-gchq-encryption-codes-security
>   09. http://secushare.org/comparison
>   10. 
> http://crypto.stackexchange.com/questions/10493/why-is-tls-susceptible-to-protocol-downgrade-attacks
>   11. http://en.wikipedia.org/wiki/man-in-the-middle%20attack
>   12. https://en.wikipedia.org/wiki/Forward_secrecy
>   13. http://www.heise.de/tr/artikel/Die-Krypto-Apokalypse-droht-1942212.html
>   14. https://en.wikipedia.org/wiki/Elliptic_curve_cryptography
>   15. http://www.wired.com/threatlevel/2013/09/rsa-advisory-nsa-algorithm/
>   16. https://gnunet.org/curve25519
>   17. https://en.wikipedia.org/wiki/steganography
>   18. http://secushare.org/rendezvous
> 
> P.S.
> 
> Thanks for feedback to tg, duy and especially Mr Grothoff.
> 
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> -- 
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> 
> US: +1-857-891-4244 | NL: +31-657086088
> site:  jilliancyork.com | twitter: @jilliancyork 
> 
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