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 transparent keying. But that's belied by the fact that, with a very few exceptions (that probably prove the rule), cryptosystems aren't directly attacked by most adversaries... except the global adversary.

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.

There is a lot wrong with PGP! It is reasonable to want it to die. But PGP is the only trustworthy mainstream cryptosystem we have; I mean, literally, I think it might be the only one.