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What's the matter with PGP?

blog.cryptographyengineering.com

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Re: What's the matter with PGP?

#101

Post by ownagefool »

unimpressive wrote: post #12
tptacek wrote: post #3

At one point in this essay, Matt suggests that every successful end-to-end encryption scheme has employed transparent (or "translucent") key management. What he's referring to is the idea behind, say, OTR: two people can use it without the key handshake required by PGP. Matt is wrong about this. He's being victimized by a pernicious fallacy. It certainly appears that the most "successful" cryptosystems have transpare…

>They do indeed have an advantage in deployability! Deployability is worth more than might be immediately obvious. The question of deployment is directly related to the business of availability . If 99% of people used a crypto system that provided no real security beyond thwarting a global adversary, which also had the option for further measures to confirm identity when necessary, we would be in a much better positi…

As a 'computer Person' my response is much the same.

You can however get them to consider what they put in there by explaining "email is like a postcard; everyone who touches it can read it".

Re: What's the matter with PGP?

#102

Post by antihero »

matthewdgreen wrote: post #34
tptacek wrote: post #6

Earlier quoted context omitted.

Both of these statements can't possibly be true: * PGP is only trustworthy if both parties treat key management with the utmost severity. * Transparent key management systems that rely entirely on heuristics and click-through warnings are trustworthy.

Really they can both be true. They're just true for different constituencies. The vast majority of users are not targeted by active attacks, nor should they have reason to be. They may be hacked or subpoenaed after the fact.

I thought that "active" attacks is exactly what we were trying to guard against?

Re: What's the matter with PGP?

#103

Post by erikb »

matthewdgreen wrote: post #30
tptacek wrote: post #3

At one point in this essay, Matt suggests that every successful end-to-end encryption scheme has employed transparent (or "translucent") key management. What he's referring to is the idea behind, say, OTR: two people can use it without the key handshake required by PGP. Matt is wrong about this. He's being victimized by a pernicious fallacy. It certainly appears that the most "successful" cryptosystems have transpare…

Hi Thomas. I used to think this way too. I think this is certainly a fine way to think about things if your goal is to keep encrypted email deployment limited to the 3-4% of email users who are either technical experts with nothing to say and/or people who are sending obviously sensitive documents. It doesn't scale much beyond that. Moreover, I would argue that a 'translucent' key management infrastructure /can/ be b…

You must worry by yourself if the key from the other person is trustworthy. If you let the software do it, you need to trust the software developers, the software providers (how did you install the software?), etc. Therefore taking key management out of the hands of the users might increase usability, but it automatically decreases security.

Re: What's the matter with PGP?

#104

Post by motters »

Good article. However if your adversary is a three or four letter agency then by all accounts it seems that PGP/GPG still does work. Snowden and Greenwald used it, apparently successfully after some tuition.

The article also doesn't mention Bitmessage, which addresses a lot of the concerns. Bitmessage isn't forward secret though.

Re: What's the matter with PGP?

#105

Post by aianus »

beagle3 wrote: post #23
rmoriz wrote: post #19

In my opinion, mail crypto needs to become mainstream usable. E.g. even trivial contents should be encrypted by default and this should be usable by default. Currently, S/MIME does a better job than PGP. While the CA-model seems to be broken in most X.509 use cases, like TLS/SSL, where a duplicate certifcate can be used to do a man-in-the-middle-attack, this does not really affect S/MIME, especially after both partie…

The "global CA" model is bust. How it was ever considered usable is beyond me, but we now have more than a decade of experience seeing just how bad it is. It is utterly, fundamentally broken and easily subverted by state actors. For now, the only reasonably usable secure key exchange method seems to be what WhisperSystems are doing on their phone app (safe against MITM if the parties know each other, and very hard to…

What's wrong with blockchain based solutions like namecoin?

Re: What's the matter with PGP?

#106

Post by beagle3 »

aianus wrote: post #105
beagle3 wrote: post #23

Earlier quoted context omitted.

The "global CA" model is bust. How it was ever considered usable is beyond me, but we now have more than a decade of experience seeing just how bad it is. It is utterly, fundamentally broken and easily subverted by state actors. For now, the only reasonably usable secure key exchange method seems to be what WhisperSystems are doing on their phone app (safe against MITM if the parties know each other, and very hard to…

What's wrong with blockchain based solutions like namecoin?

If I understand correctly, namecoin is a distributed DNS replacement. Is there a way it addresses impersonation (e.g. MITM?), if so, can you please point me at documentation?

DNS does not address it, and even DNSSEC does not (if you can forge the certificate, and you can mitm the traffic - which state actors are all capable of - then it doesn't matter that you can't forge the DNS response itself).

Re: What's the matter with PGP?

#107

Post by sorbits »

tptacek wrote: post #3

At one point in this essay, Matt suggests that every successful end-to-end encryption scheme has employed transparent (or "translucent") key management. What he's referring to is the idea behind, say, OTR: two people can use it without the key handshake required by PGP. Matt is wrong about this. He's being victimized by a pernicious fallacy. It certainly appears that the most "successful" cryptosystems have transpare…

> […] with a very few exceptions (that probably prove the rule)

Off topic and pedantic but exceptions do not prove rules.

A specific exception like “you are allowed to do X when Y is true” may be used as proof of an (unwritten) rule about X being forbidden.

I.e. here we use the exception (when Y is true we are allowed to do X) to prove that there is a general rule saying that X is forbidden.

Re: What's the matter with PGP?

#108

Post by perlgeek »

Can forward secrecy even work for emails, where you don't have a bidirectional communication channel? (Maybe the answer is "You have to build that bidirectional communication channel", but that means such a system can't simply use mail, it has to use mail plus X).

Re: What's the matter with PGP?

#109

Post by warcode »

keybase.io and the mailvelope browser plugin both do fine work in making PGP simple to use.

It isn't about being NSA-proof, its about having the volume of "Enveloped"/PGP encrypted emails be so high that it isn't possible to directly target everyone.

Re: What's the matter with PGP?

#110

Post by muyuu »

These are largely problems with email, not PGP - which btw is not just by email, in fact I almost never use it with email.

SMTP is not meant to be secure. You insist in communicating through an insecure channel-protocol and making it secure as an afterthought, and it's always going to be inconvenient or otherwise suck. I say PGP is pretty good at what it does, and it's nice in that it doesn't promise what it doesn't do.

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