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What's the matter with PGP?

blog.cryptographyengineering.com

111–120 of 166 posts

Re: What's the matter with PGP?

#111
post #97

Why isn't RFC 1751 http://www.ietf.org/rfc/rfc1751.txt used to provide the fingerprints that are readable? Verifying would be much more convenient than now. "For example, the 128-bit key of: CCAC 2AED 5910 56BE 4F90 FD44 1C53 4766 would become RASH BUSH MILK LOOK BAD BRIM AVID GAFF BAIT ROT POD LOVE Likewise, a user should be able to type in TROD MUTE TAIL WARM CHAR KONG HAAG CITY BORE O TEAL AWL as a key, and the ma…

I haven't used the "original" PGP program for a very long time, but IIRC it had the option to use RFC 1751 or a similar scheme. A quick web search finds to options to use this scheme in GnuPG. Strange!

Re: What's the matter with PGP?

#112
post #66

Learning to drive a car is hard. You have to watch the road, coordinate hands and feet, anticipate other drivers' moves and so on. No one bats an eye about this, because "it's a skill you have to learn". If you don't play by the rules of the road, you'll end up killing someone, or getting killed. But for some reason (maybe because it's generally less life-threatening), people seem to expect deeply complex subjects, l…

It is a matter of skills which people find useful.

Learning to fly a plane is much harder than learning to drive a car, and almost no-one learns how to fly a plane because it just isn't a useful skill for most people.

I did spend time learning all about PGP, and I wish I hadn't bothered, as the skill of learning PGP has zero value to me. On the other hand, learning to drive a car, which took longer, is much more useful.

Re: What's the matter with PGP?

#113
post #105

Earlier quoted context omitted.

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).

You can place your own self-signed public key in your namecoin record. There is no longer any need for certificate authorities which can be coerced into forging certificates.

Re: What's the matter with PGP?

#114
post #52

Earlier quoted context omitted.

Either you need a trusted third party or you need to pass something that looks like (at best): 4UpbRAXYMgrESrAwiLPYymNNni1hwyL2JEK7zz2SN52t You could do that by printing it on a business card or reading it over the phone, and then the other guy is going to have to type it in somewhere. The reason trusted third party keeps on coming up, despite all the myriad fundamental problems, is exactly because slinging that arou…

I've seen business cards with PGP fingerprints encoded as QR codes. That's a pretty neat idea.

Except you never notice when someone switches the QR code, as Tomte says.

Re: What's the matter with PGP?

#115
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…

> In the absence of routine attacks targeting cryptography, it's easy to believe that systems that don't annoy their users with identity management are superior to those that do. They do indeed have an advantage in deployability! But they have no security advantage. We'll probably find out someday soon, as more disclosures hit the press, that they were a serious liability.

You're probably talking about the PKI here. However, after a year's worth of Snowden leaks (and perhaps other leakers too) there have been zero documents discussing routine or even occasional sabotage of the PKI.

You suggest that we'll "probably" find out "someday soon" that only PGP works and everything else sucks, but we already went through that acid test. PGP was such an epic failure Snowden and Greenwald failed to connect entirely, and there were no big reveals about certificate authorities.

That doesn't mean the CA system is infallible, just that attacking endpoint security is easier. But as Matt's GPG example shows, GPG endpoint security is just as pathetic. Heck I didn't realise that GPG couldn't safely import public keys by fingerprint. How the hell does software like that, which has been around so long, fail to do such a basic check? QUANTUM would have made mincemeat of anyone trying to communicate securely using mainstream PGP implementations, whereas most S/MIME implementations I know of wouldn't have been fooled so easily.

Hand-waving about how anything other than PGP is trustworthy doesn't fly with me: there's too much real world evidence from real world adversaries that it sucks and other systems work better.

Re: What's the matter with PGP?

#116
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…

Comodo give away free S/MIME certs:

http://www.comodo.com/home/email-security/free-email-certifi...

They can be generated and installed into the OS keystore by your browser automatically. By the low standards of crypto it works pretty well. Any old email client supports it out of the box.

Re: What's the matter with PGP?

#117
PGP is about identity and privacy. We are not going to get that from Email. Email isn't worth fixing. Its time to move on.

In the last few years we have seen IM and SMS merge into an almost seamless experience. Surely we could engineer a UI that also copes with larger bodies of text at the same time?

We need clients or servers that are multi-protocol. That way we can experiment with new ways of communicating.

Re: What's the matter with PGP?

#118
post #55
post #32

Earlier quoted context omitted.

It's not doable, because there are major unsolved problems. Protection of a private key, for example. The only outcome of such a chart would be reams of people utterly vulnerable and thinking that they are not. If you constrain the environment, e.g. "How to use SSL certificates in Chrome on Mac OS X Lion" then there might be a chance that could fit on one page in an easy to understand format.

> Protection of a private key, for example. I have a master key that was created offline, and use a subkey on a usb smart token. It works good but it was a bitch to set up. Apparently Qubes OS has a hardware-virtualized PGP container for protecting private keys, but that's not a viable solution right now.

The offline masterkey stored on an encrypted medium is the approach that makes most sense. This[1] guide is pretty decent, and somewhere on the Debian wiki is essentially the same information (but less nicely presented).

The OP's complaints boil down to two IMO: 1) poor UX; 2) trust is difficult to manage.

1) Seems solvable to me again with subkeys for encryption and signing (which I believe are created by default for GPG2.0 anyway).

2) Asking technology to solve the problem which only each individual can answer ("do I trust this person to be evaluate other people's identities as carefully as me?") is not doable.

The example of someone getting a journalist's pubkey and being stung by the (fixed) bug whereby the wrong key may be imported is again letting the user off the hook. If someone is not actually using GnuPG's abilities to examine the WoT and see who has signed the journalist's key etc then it's an example of magical thinking with "encryption" replacing any other nostrum.

I don't believe that problem can be solved with technology.

1. https://alexcabal.com/creating-the-perfect-gpg-keypair/

Re: What's the matter with PGP?

#119
post #98

Earlier quoted context omitted.

Why is it not easy to verify a key (fingerprint)? Put it on a business card with the email address or read it over the phone? Also, DNSSEC isn't much more secure than our current CA system.

Now your collection of business cards is susceptible to tampering (no cryptographic authentication!). Do you never leave your collected business cards unattended at a conference or trade fair? Possible, if you put them into your shirt pocket. Do you store them in a vault lomg-term? Probably not. Is it impossible to impersonate you, either with a human sound-alike or by voice generation software? If you want perfect s…

"Now your collection of business cards is susceptible to tampering (no cryptographic authentication!)."

You are missing the part where it was suggested that the recipient of the business card telephones you and asks to verify the fingerprint.

Re: What's the matter with PGP?

#120
post #98

Earlier quoted context omitted.

Now your collection of business cards is susceptible to tampering (no cryptographic authentication!). Do you never leave your collected business cards unattended at a conference or trade fair? Possible, if you put them into your shirt pocket. Do you store them in a vault lomg-term? Probably not. Is it impossible to impersonate you, either with a human sound-alike or by voice generation software? If you want perfect s…

"Now your collection of business cards is susceptible to tampering (no cryptographic authentication!)." You are missing the part where it was suggested that the recipient of the business card telephones you and asks to verify the fingerprint.

You are missing both the "or" in his sentence (i.e. he describes alternatives, not cumulative measures) and my retort to the verification by phone.
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