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I'm giving up on PGP

blog.filippo.io

221–230 of 350 posts

Re: I'm giving up on PGP

#221

People who use PGP keys, can you give examples of your use? I'm genuinely curious. Who are you contacting, or who is contacting you? The author says he only receives 2 encrypted emails a year. Not only do I not have a PGP key, I don't think I've ever found myself in a situation where it was even an option to use one.

1. Reporting vulnerabilities

2. Signing git commits/tags

Re: I'm giving up on PGP

#222
post #93

I guess this is a good opportunity to review Matthew Green and Moxie's posts on PGP, too: https://blog.cryptographyengineering.com/2014/08/13/whats-ma... https://moxie.org/blog/gpg-and-me/

I really like what moxie wrote here. There is a big difference from the best thing and the thing that can actually exist in the real world right now.

Re: I'm giving up on PGP

#223

The conclusions here (avoiding long-lived per-identity keys and having the option to easily rotate and re-validate per-device keys) are very much what we've aimed for in the end-to-end crypto for Matrix.org ( https://matrix.org/blog/2016/11/21/matrixs-olm-end-to-end-en... ). Rather than using a silo like Signal or WhatsApp, it is possible to get the flexibility of an open federated network built on an open standard,…

IMHO, the biggest issue with matrix, is that there's no free hosted solution for using my own domain/email. Sure, I can rent a server and set up my own, but that's a huge commitment to "try out" a protocol which non of my acquaintances uses yet.

hm, can you point me at an email provider who provides free SMTP/IMAP/webmail or XMPP hosting for custom domains? I may be missing something, but I can't think of one...

The model is that you can try it out on the matrix.org server via riot.im or something, and then run your own if you like what you see :)

Re: I'm giving up on PGP

#224
Summary: The author decided that being connected to long term keys does more harm than good, partly due to the pressure to stay with potentially compromised keys due to the difficulty of starting over. The author will instead focus on secure IM using short term keys bootstrapped by social media accounts.

1) As others have pointed out, I really think the author is overestimating the effort required to compromise a twitter or other social media account. There are many accounts of this happening, including to people like Brian Krebs who knows he is a target and does everything possible to avoid the attacks.

2) Encrypted IM as the primary higher security communication channel seems to be a popular option these days, mostly leaving those of us who don't like IM to look at alternatives.

3) Briar (briarproject.org) is a promising alternative for messaging, although not ready yet and currently only targeting android, which has its own major security issues. Due to the focus on enabling offline, forward secure messaging, it can be used to defeat mass (network) survailance. It can also be used online and addresses some of the specific concerns raised.

4) General purpose computers are both handy and necessarily have security issues. Special purpose devices for more limited secure communication would help with many issues.

5) Secure communication isn't much of a goal; it is more helpful to consider specific threats. If you do something non-trivial towards a vague goal, it is easy to find a way it doesn't meet that goal when you feel like not doing it any more. I'm not sure what the author was trying to achieve with PGP in the first place.

Re: I'm giving up on PGP

#225

Summary: The author decided that being connected to long term keys does more harm than good, partly due to the pressure to stay with potentially compromised keys due to the difficulty of starting over. The author will instead focus on secure IM using short term keys bootstrapped by social media accounts. 1) As others have pointed out, I really think the author is overestimating the effort required to compromise a twi…

Kind of off topic: I really like iMessage. Not to be an Apple fanboi, but it really is one of those things where It Just Works(tm). Encryption shouldn't have to be something the end user has to worry about; it should be transparent to the user while still being as secure as possible (HTTPS and TLS are a great example of this). For the user who cares about encryption, they don't have to configure anything. For the user that doesn't care, they still benefit.

By baking it into the OS, Apple ensures that anyone with an iDevice benefits from it. Compare that to having to download an app that may change depending on possible compromises. Anyone who's tried to convince a family member to use Signal, Telegram, etc. knows how much of a pain it is.

Re: I'm giving up on PGP

#226
My ongoing concern is around where reasonable alternatives fit in.

- Securedrop, where users upload messages and they are automatically encrypted

- Darknet services

- Businesses where users communicate via desktops.

Signal/ etc works in a different space and doesn't provide an alternative to these.

Re: I'm giving up on PGP

#227

Earlier quoted context omitted.

I have to partially disagree with that. Calling PGP an utter failure is an understatement. Just like calling a cat a small tiger. PGP is possibly the WORST experience in usability for any well known software that ever lived. This thing should be taught in courses for decades to come as how to fail a product by 1) having no UI 2) no integrations with anything 3) zero usability 4) not even trying to give a fuck about n…

Why the fuck would you ever insert a government-provided USB key into any computer you actually cared about, much less actually use any government-provided key? The national government is the prime adversary . I mean, seriously, Alice and Bob want to communicate, and your solution is that they should use Eve as a courier!??

FWIW: your point--and it's a good one--is better made without the yelling.

And to answer you, though I don't speak for the person you were relying to: the U.S. government isn't even in my threat model. If the Eye of Sauron points my way, I lose. And so, given that as a prior, a universally trustable third party is not a bad idea. The implementation might totally suck (and I think it's a better practice to have a wide set of vendors and making the acquisition of such a key subsidized, rather than directly provided, by the .gov), but the central point of trust doesn't, and it isn't inherently a problem for it to be state-operated.

Re: I'm giving up on PGP

#228
post #32

Earlier quoted context omitted.

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. I don't think the "WoT" is conceptually flawed, and frankly, the argument that "people of average intelligence" can't grasp the concept comes from a very high horse and is also untrue. It's simply that any and all software for PGP utterly fails in the UX and functionality department when it comes to key management. Web of Tr…

I have to partially disagree with that. Calling PGP an utter failure is an understatement. Just like calling a cat a small tiger. PGP is possibly the WORST experience in usability for any well known software that ever lived. This thing should be taught in courses for decades to come as how to fail a product by 1) having no UI 2) no integrations with anything 3) zero usability 4) not even trying to give a fuck about n…

> Just get the national government to distribute RSA USB keys to every citizen.

I lived in a country that did exactly that. And it was a disaster. The keys were trivially easy to steal, even by accident (personal experience here), and you still have the same trust problem as before, except that with a central authority now you do not have as much control.

I have also used the electronic-signature-comes-with-your-ID-card thing, and it was a similar disaster, with dodgy drivers and half-arsed crypto implementations in common software. E.g., try using the same token in Firefox and Thunderbird (or anything else) at the same time.

PGP is fine. It's just that proper security is not easy. And the same applies in the physical world as much as in computing.

Re: I'm giving up on PGP

#229
post #32

I find very interesting the point about the split between what WoT was supposed to be, in theory, and what little it represents, in practice, in terms of practices about key verification. It has been said many times that the lack of adoption of pgp in mail was due to the average user not being able to grasp the concepts behind the proper operation for key management, but the article points to common practices among "…

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. I don't think the "WoT" is conceptually flawed, and frankly, the argument that "people of average intelligence" can't grasp the concept comes from a very high horse and is also untrue. It's simply that any and all software for PGP utterly fails in the UX and functionality department when it comes to key management. Web of Tr…

The web of trust is fundamentally flawed and for very simple reasons.

First of all, the WoT is based on belief networks. What is a belief? Is it based on a probability? Is it binary? Can we believe something negatively? Whatever it is, we know it is subjective and difficult to define quantitively.

Second of all, even when formally specifying a belief using a certain quantity, we need to calculate transitive beliefs (person A beliefs with certainty x the identity of person B, C and D, who each believe with certainty y the identity of person E and A). This requires doing some matrix inversions for which the whole matrix needs to be known. However, who do we trust to provide us with the matrix? If I can provide the matrix, I can also tamper by adding extra nodes, thus shifting trust towards nodes I control. We can provide the matrix in a distributed fashion, but how do we prove completeness?

Then there is a temporal aspect to WoT which is hard to tackle. I might have a belief now, but that does not entail I will belief it tomorrow. Without a continuous stream of events on a subject, the precision of my beliefs are always diminishing. However, the current WoT networks do not take this fully into account (or transitive beliefs for that matter).

Re: I'm giving up on PGP

#230

I find very interesting the point about the split between what WoT was supposed to be, in theory, and what little it represents, in practice, in terms of practices about key verification. It has been said many times that the lack of adoption of pgp in mail was due to the average user not being able to grasp the concepts behind the proper operation for key management, but the article points to common practices among "…

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. IMO, the idea, the model, and implementation are flawed. The idea that people care about a web of trust in general is bad. The model itself relies on the assumption that it's a popular piece of software that is used in the way it's intended. PGP itself is popular, but only for the fact that viable alternatives are thin. The…

> The idea that people care about a web of trust in general is bad.

Well, the very question is kind of a type error: people don't know what a computer is in the first place. 1 in 4 can't use computer in any capacity, and 90% of the rest have zero knowledge of the underlying principles. They don't even know if they would care about a web of trust.

In the mean time, the powers that be are building us a network of universal spying. Oh well.

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