Cryptography engineers have been tearing their hair out over PGP’s deficiencies for (literally) decades. When other kinds of engineers get wind of this, they’re shocked. PGP is bad? Why do people keep telling me to use PGP? The answer is that they shouldn’t be telling you that, because PGP is bad and needs to go away.
There are, as you’re about to see, lots of problems with PGP. Fortunately, if you’re not morbidly curious, there’s a simple meta-problem with it: it was designed in the 1990s, before serious modern cryptography. No competent crypto engineer would design a system that looked like PGP today, nor tolerate most of its defects in any other design. Serious cryptographers have largely given up on PGP and don’t spend much time publishing on it anymore (with a notable exception). Well-understood problems in PGP have gone unaddressed for over a decade because of this.
Two quick notes: first, we wrote this for engineers, not lawyers and activists. Second: “PGP” can mean a bunch of things, from the OpenPGP standard to its reference implementation in GnuPG. We use the term “PGP” to cover all of these things. //
If we’ve learned 3 important things about cryptography design in the last 20 years, at least 2 of them are that negotiation and compatibility are evil. The flaws in cryptosystems tend to appear in the joinery, not the lumber, and expansive crypto compatibility increases the amount of joinery. Modern protocols like TLS 1.3 are jettisoning backwards compatibility with things like RSA, not adding it. New systems support just a single suite of primitives, and a simple version number. If one of those primitives fails, you bump the version and chuck the old protocol all at once.
If we’re unlucky, and people are still using PGP 20 years from now, PGP will be the only reason any code anywhere includes CAST5. We can’t say this more clearly or often enough: you can have backwards compatibility with the 1990s or you can have sound cryptography; you can’t have both. //
This isn’t going to get fixed. To make actually secure email, you’d have to tunnel another protocol over email (you’d still be conceding traffic analysis attacks). At that point, why bother pretending?
Encrypting email is asking for a calamity. Recommending email encryption to at-risk users is malpractice. Anyone who tells you it’s secure to communicate over PGP-encrypted email is putting their weird preferences ahead of your safety.
