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[liberationtech] the 14th reason not to start using PGP is out!

carlo von lynX lynX at
Sun Nov 24 08:22:33 PST 2013

On Fri, Nov 22, 2013 at 09:03:14PM +0000, Tempest wrote:
> no. i was pointing out that you expect the tech to provide a function
> for which it was never intended. if you want anonymity, encrypt your
> hard drive and install one of the many flavors of operating systems that
> are powered by tor. then, create your pgp keys after that and host it on
> a .onion.

Hmmm.. if you're anonymous, then you don't have friends to email with...
so what do you need a mail address for? And if you hand out your brand
new torified email address to your friends, you are no longer *really*
anonymous since your social graph reveals to a certain extent who you
are. After all, your friends will be too lazy to follow your lead into
torland if they don't have to.

> > No, all they need is to start using a software that does all of that
> > BY DEFAULT and there is no way to do it wrong BY DESIGN.
> lol! and what is such a tool? you seem to think pond is the current

Pond, Cables, Bitmessage, Susimail, Briar, I2PBote.. even RetroShare
does that part right.

> answer. tell us what pond servers are reachable by anyone using the
> standard old e-mail system. you ignore that obvious problem that users
> are going to have with somehting like pond. since you've ignored it
> multiple times now, you can create anonymous e-mail accounts over tor.

Yes, it's about time I respond to this fallacy, but I first had to
understand why you would want to do that.

> you can encrypt those e-mails with pgp. it's a good secure design which
> still allows people who don't use pond to be able to reach you.

So you think that hiding your own traces, but leaving all the rest of
the social graph out there in the open is a good idea. Well, maybe it's
better than nothing, but the more you practice this, the more I guess
that even automated software can figure out what your former e-mail
address was, thus who you are.

> additionally, perhaps you missed this from the pond developer?

I am very thankful that Pond forces people to switch to a sane new
mail system. If you want to talk to me, you have to install it - this
is good for all participants, while requiring people to install PGP is
totally insufficient to fulfill your civic duty to not be a predictable

> "So Pond is not email. [...] Dear God, please don't use Pond for
> anything real yet. I've hammered out nearly 20K lines of code that have
> never been reviewed. Unless you're looking to experiment you should go
> use something that actually works."

If you read the 14 reasons they conclude that we have to review all the
alternative options to e-mail ASAP since insisting on PGP is causing
more harm than using new software. The IMAP failure is just an example
on how software developers can be overburdened with responsibility for
the far too complex architecture that e-mail/PGP has become. And the
idea that my grandpa would be responsible if his Thunderbird comes
configured with IMAP on Gmail is surreal. UX experts to the rescue!

> > This is all too complicated for people to even grasp let alone follow
> > and I bet half of the points in the 14 reasons still apply also to this set-up.
> > I leave it as an exercise to an interested reader to check.
> no, it really isn't. you use tor for your network connectivity and you
> use gnupg for e-mail encryption.

Now that I understand how serious this is to you, I will answer fully.
Let's check with ... still applicable in any case:

    1. Downgrade Attack: The risk of using it wrong.
    8. PGP conflates non-repudiation and authentication.
    10. Workflow: Group messaging with PGP is impractical.

Applicable unless you only talk to people who themselves
use the same mail server on the Tor network:

    2. The OpenPGP Format: You might aswell run around the city naked.
    3. Transaction Data: Mallory knows who you are talking to.
    6. Federation: Get off the inter-server super-highway
    7. Discovery: A Web of Trust you can't trust.
    9. Statistical Analysis: Guessing on the size of messages.
    12. Overhead: DNS and X.509 require so much work.
    14. The Bootstrap Fallacy: But my friends already have e-mail!

Points solved, if you can trust the mail server:

    4. No Forward Secrecy: It makes sense to collect it all.
    5. Cryptogeddon: Time to upgrade cryptography itself?
    11. Complexity: Storing a draft in clear text on the server
    13. TL;DR: I don't care. I've got nothing to hide.

The question remains... how can you trust a mail server
not to store all of your PGP or pass it on to Mallory?

Points solved in any case:


In practice I don't find that a score worth making festivities about.
Pond currently only fails me on point 10.

> > That's why neither Pond nor Susimail nor RetroShare nor TorChat nor Bitmessage
> > store any clear text data on any servers! (How many more tools do I have to list
> > to make you see that there is plenty of ferment in the scene of future
> > communication tools?)
> list as many as you want. you fail to understand that a compromised
> system renders any protections they may provide moot. use of gpg,

Anyone who runs Android, iOS, Windoze or Intel AMT hardware can be
a subject of a targeted attack. That's outside the scope of this
exercise. I am trying to get the large majority of the population
protected, not bullet-proof against targeted criminal investigation.
Talk to the Whonix guru if that is your priority (great job, btw).

> > Actually it's not. It took them quite some effort to find silkroad and it
> > probably didn't even involve tracing Tor - at least there is no proof of
> > that. I think any federated social web software is a better example of
> > how servers get you compromised because of
> you don't even understand what i was talking about. everyperson on that
> site who uses gpg to encrypt their communications between each other
> didn't have to worry about a knock on their door from the authorities as
> a direct result of providing a buyer or seller with their address. the
> site was compromised and, as a direct result, people who did not encrypt
> their communications were located. how the site was compromised is
> unimportant. the fact is that those who uses something like pgp were not
> immediately compromised, if compromised at all.

Oh alright, again a scenario that has nothing to do with what I was
talking about, that's why I didn't think you seriously wanted to
discuss this.

Of course it is wildly dangerous to have unencrypted communications
on a website. The fact that the website hides its location behind a
.onion doesn't make that any better. When I say that technologies like
Tor can make something like Pond possible I don't mean that you can
use it also in a completely wrong way and expect the same results.
It's like saying PGP isn't safe if you sign your mails instead of
encrypting them, or saying that traffic lights make accidents impossible.

> > Unless they get at your private key. 
> duh.

What. It's true. If by your social graph they figure out who you are
and get at your laptop they can (a) decrypt everything that was sent
to you on silkroad and (b) possibly have digital proof of your

> > Why are we talking of servers that have all the messages in cleartext?
> because you and another user signed on to the silly notion that one
> didn't need to use encryption on a server within the tor network. i
> provided a very real world example on why you should.

You must be mistaken. Websites behind .onion aren't in any way a safer
visit - in fact they are more likely to host malware for obvious reasons.
I stated dozen times before that PGP is better than nothing, especially
if you are going to engage in conversations on some remote website that
stores all data in the clear. So I certainly didn't (mean to) say that.

Everybody else: excuse me if I skip replying, but I don't have the
impression that there's any further scientific debate to be made there.

P.S. Yosem, thanks, excuse me for bringing up emotional subjects.
Hope having this catharthis is within the purposes of libtech, anyhow.

For now I'm just asking for awareness and a change of mentality in the
community.. and within half a year I'd like to see SMTP-free mail take
off for real. Start rewriting your crypto manuals and brochures, please.

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