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What's the matter with PGP?

blog.cryptographyengineering.com

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Re: What's the matter with PGP?

#71

Post by graycat »

> If the NSA is your adversary just forget about PGP.

Why? Last I heard, breaking PGP was equivalent to being able to factor large integers into a product of prime numbers. So, NSA is able to do that, and no one else can, no one in the public heard about it, no university research mathematician published about it, NSA has mathematicians who figured out how to do that but their major profs back in grad school don't know how, no one got a Fields Medal for it, etc.? I don't believe that.

What's going on here?

He means I need a Faraday cage? Okay, tell the NSA I have one; put it in place this afternoon.

He means the NSA has trained cockroaches that can wiggle into my hard drives while I sleep and steal all my data? If so, then fine. I'll spray bug killer.

Otherwise, why should I believe that the NSA could crack my PGP encrypted e-mail?

Re: What's the matter with PGP?

#72

Post by aestetix »

I'm kind of sad the author didn't touch on key signing at all. The trust levels are basically meaningless. What does it mean to trust someone more than someone else? If doing a request to get someone's key exposes your social network, imagine what publicly signing someone's key does. Just some food for thought :)

Re: What's the matter with PGP?

#73

Post by XorNot »

_delirium wrote: post #44
bad_user wrote: post #40

Earlier quoted context omitted.

If a global adversary can do it, then it is only a matter of time before a local crime syndicate can do it as well, after all stealing credit cards and other sensitive info is a booming business. And what really bothers me is that this will give people a false sense of security. At least right now I'm seeing regular folks refraining from exposing sensitive info online out of fear of evil hackers that are often the su…

I agree, and I think that's especially a good argument for email. For mail submission at least, I think most users for that use-case are now either using or moving to encrypted SMTP AUTH with certificate checking, which should be fairly robust on the local side (between you and your ISP/company), modulo the problems that exist with the CA system. For IM though I think lots of people are more worried about embarrassme…

You need end-to-end encryption anytime the IM server isn't under your control. It's a reasonable assumption that if they could log everything, some manager somewhere has ordered them to do it regardless of legality.

Re: What's the matter with PGP?

#74

Post by XorNot »

junto wrote: post #42

I'm using TextSecure on my Android phone as a Messaging replacement and it is great. However it appears to me that the service is not decentralised in any way. Is that assumption correct? I like the email model such that anyone can install and run an email server. I'd actively push friends, family and colleagues to use a decentralised email replacement that was as easy to use and secure as TextSecure.

I don't trust TextSecure. It's too transparent. It is entirely unclear what happens if it can't send an encrypted message. It's unclear where and how much I'll be billed (important to those of us outside the US). And sans user authentication, there's no real trust model there.

Re: What's the matter with PGP?

#75

Post by _delirium »

XorNot wrote: post #73
_delirium wrote: post #44

Earlier quoted context omitted.

I agree, and I think that's especially a good argument for email. For mail submission at least, I think most users for that use-case are now either using or moving to encrypted SMTP AUTH with certificate checking, which should be fairly robust on the local side (between you and your ISP/company), modulo the problems that exist with the CA system. For IM though I think lots of people are more worried about embarrassme…

You need end-to-end encryption anytime the IM server isn't under your control. It's a reasonable assumption that if they could log everything, some manager somewhere has ordered them to do it regardless of legality.

If the threat you're trying to protect against is your local IT sysadmin eavesdropping on your conversations about office politics, the fact that Google Talk may internally log your IMs is close to irrelevant. The NSA might be able to get those logs from Google, but your coworkers probably can't.

Re: What's the matter with PGP?

#76

Post by bascule »

graycat wrote: post #71

> If the NSA is your adversary just forget about PGP. Why? Last I heard, breaking PGP was equivalent to being able to factor large integers into a product of prime numbers. So, NSA is able to do that, and no one else can, no one in the public heard about it, no university research mathematician published about it, NSA has mathematicians who figured out how to do that but their major profs back in grad school don't kn…

If the NSA can't attack the crypto (not saying they can, but maybe) they'll attack endpoint. Systems like QUANTUMINSERT allow them to selectively MitM your plaintext HTTP connections, directing your browser to load some asset that exploits a browser vulnerability, and using that to install persistent malware.

Re: What's the matter with PGP?

#77

Post by XorNot »

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…

I don't understand why we don't just apply the OTR model to email.

OTR's big latency is the initial handshake. After that, you can persist the session. But email is intrinsically a high latency medium anyway! We can afford 1 or 2 days delay to setup an initial encrypted connection. In fact, we can display a big "not encrypted!" message to users, while still letting them exchange email, until we've done the handshake and socialist millionaire protocol (or verified keys by some other means) setup.

I am willing to bet like 70-80% of people who send email to each other physically have their email clients online at the time they do it, even if they take a lot longer to answer - especially with the number of smartphones out there. So we can setup an OTR session after 1 message the vast majority of the time, and then reuse the same session as much as possible.

Re: What's the matter with PGP?

#78

Post by MrUnknown »

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…

> I challenge you to go explain to anyone you know who does not identify as a 'computer person' how email routing works

I usually use the "It's like mailing a postcard" comparison.

Re: What's the matter with PGP?

#79

Post by Spooky23 »

matthewdgreen wrote: post #33
Spooky23 wrote: post #11

Earlier quoted context omitted.

You nailed it. I stopped reading and started laughing when iMessage was hailed as a successful platform addressing these issues. The only thing securing iMessage is the procedure for processing law enforcement requests. PGP is a tool that requires expertise to operate effectively. That isn't good or bad, it just is.

I think if you read it that way you probably didn't click the link to the extensive criticism I've written about iMessage's key distribution. Saying something is better than plaintext is not the same as saying it's good enough to send secret documents. http://blog.cryptographyengineering.com/2013/06/can-apple-re...

I'm not terribly familiar with your writing, but I disagree that plaintext is inferior to ineffective crypto. The problem with convenient things is that you are giving up control in exchange for expediency.

In my professional life, I've provided communications solutions to a variety of true VIPs in key executive and other roles. The advice that their counsel gave on most occasions was simple: exchange secrets orally, and in person.

That means don't use the courthouse wifi, don't conduct critical deliberations via email or public telephone networks. If you google around, you can see plenty of referenced to US state governors only communicating via Blackberry text or obscure phone lines, mostly to control short term leaks and keep deliberations out of the public record.

The point of all of this is that keeping secrets is hard, and if you must exchange them electronically, you need a strong set operational protocols to keep those secrets.

Re: What's the matter with PGP?

#80

Post by alaaibrahim »

> Now let's ignore the fact that you've just leaked your key request to an untrusted server via HTTP. This is a public Key, so secrecy it's not needed here, also he is providing the Fingerprint on another location, so if there was a MITM attack, it should happen on both twitter (HTTPS) and pgp.mit.edu
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