[tptacek]

This is not normal. Modern cryptosystems don't have anything like PGP's insane "packet" format, which has caused other problems before this. There's no principal of design that would lead you to what PGP came up with, and the only reason we still have to deal with it is path dependence. I don't even care if you call the next design "PGP2", just throw this system in the bin and start over.

[mananaysiempre]

Unfortunately, modern cryptographers refuse to design systems for confidentiality of store-and-forward communications, motivated by the fact that one can provide better security in instant messaging[1] (which in most cases implies vendor lock-in). Age is one of the few systems that could accomodate email, and its author’s “solution”[2] is for the user do ASCII armor/dearmor like a caveman, which handily loses to PGP/MIME in just about every email client that supports the latter. So, until somebody does better, PGP email it is.

[1] https://blog.cryptographyengineering.com/2014/08/13/whats-ma...

[2] https://github.com/FiloSottile/age/issues/93

[tptacek]

They're right about that.

https://www.latacora.com/blog/2020/02/19/stop-using-encrypte...

But none of that excuses PGP's clanking and outmoded design. Things that are bad are bad. We can't moralize our way around that.

[mananaysiempre]

I don’t really want to make a moral argument about PGP. Yes, the design of PGP is bad even if we hold its problem statement fixed. The thing is, the people I would trust to design something better consider that problem not worth solving. So if I as a user do want a solution to that problem[1], I’m stuck with PGP, which is bad. But at least it makes an attempt.

[1] Because I need to be in areas with bad connectivity often enough that I don’t want my every communication method to require a Internet connection to be available continuously (or even daily). Because Signal’s refusal to issue me an account without a phone number (which I cannot legally obtain without tying it to my government ID) is a real risk to my personal safety, given my particular situation. Because Signal’s stance on alternative implementations and the like is a hair’s breadth away from my refusing to use it. Some of these you could call moral arguments, but none of them are about PGP, as such.

[tptacek]

The basic thesis of that post (the original of which I wrote) is that if messages are important enough that they need to be protected from state-level adversaries, then they're important enough that you shouldn't care about all the other reasons you like SMTP. If any of SMTP's affordances trump message security, you're LARPing the security part: you're protecting them in a threat model that doesn't correspond to a real-world attacker.

[jcranmer]

With email, you necessarily leak the triple (to, from, date): no matter how good your cryptosystem is, that information can be pulled from the mailserver logs (and if you don't leak that triple, spam deluge is unsolvable). As a practical matter, you generally need to leak the mail headers as well, which contains a decent amount of useful metadata as well. Now I'm not an expert on how spy agencies do their analysis, but my understanding is that the set of information that has to be leaked by email is already the most useful information for them. And that's part of tptacek's point: if your main threat adversary is state-level actors, you've already lost if you're using email simply because you're using email.

What if your threat model isn't state-level actors? Well, the baseline of email these days is that your communication and your recipient's communication to the mail servers are both encrypted with TLS. The mail servers themselves may or may not communicate with each other using TLS, but if you really care about security, you can choose a mail server which will be using TLS. In other words, email is already at a baseline state of the only people aware of the message being the sender, the recipient, and their mail admins (and whomever these people choose to leak the message to, perhaps unwillingly). Encrypting email will only remove the mail admins from the list, and even then, they can still tell anybody whom you talked about.

So the use case of encrypted email boils down to wanting to hide the contents of communication but not hiding the fact of communication itself. Which isn't a broad use case; the best examples I've found in my own life is something like financial statements, but even in those cases, there's a pretty decent workaround: send an email saying "hi, we have a document for you online in our usual secure file repository" (protected by modern, useful standards for secure files). I don't like that only because I can't automate saving those files off to my own storage for my own purposes, but that is such a niche desire that I can understand why the bank doesn't bother.

[tptacek]

The original version of this post also mentioned, and was in fact motivated by, a fatal flaw in encrypted email that everyone who has used it at scale has experienced, which is that participants will reply to encrypted messages with unencrypted responses that quote the original (whether or not a reply quotes the original doesn't change how devastating this problem is, but sort of highlights how insane the system is).

So I think the metadata argument is dispositive. I agree with you that it's difficult to compose a coherent threat model that leaves metadata exposed the way SMTP does.

But the core argument of the piece is that encrypted email makes security concessions nobody would make if e.g. the wire for the down payment on their house was at stake, or if they were organizing against an oppressive state-level adversary. If encrypted email is unsuitable for those scenarios, then it seems more important to keep it from being used there than it does to accommodate the interests of people who using it for other reasons.

[jcranmer]

I'll admit that my knowledge of signed/encrypted email is mostly from S/MIME (and underlying CMS), so I'm curious if you could enlighten me on what PGP is doing that is so much more insane than that.

[woodruffw]

Well, I don't know if I would call PGP so much more insane than CMS or PKCS#7 :-). Definitely worse, but CMS is not high up on the list of honorable cryptographic envelope designs.

On the format level, CMS has some of the same flaws as PGP: dynamic TLV encodings (BER), extension points everywhere, and a disconnect between format and cryptographic versioning. On the cryptographic level, S/MIME benefits somewhat from certificates on the Internet PKI being less of a wild west than PGP certificates, and from having a community group (the S/MIME Cert WG of the CA/B Forum) invested in strengthening S/MIME's certificate profile beyond the baseline stipulated in RFC 5280. Of course, for non-public S/MIME deployments, none of that applies.

All that said, I don't think I would treat S/MIME (or CMS, or PKCS#7) as a guiding star: EFAIL affected S/MIME too[1]. But they have the "advantage" of being bad at just their niche (signing and encryption of email), versus being bad at every niche. The latter is PGP's historic curse.

[1]: https://efail.de/

[jcranmer]

The way I've previously internalized it is CMS is bad principally because it's generic container of general generalizablity (on multiple levels, even) and the fundamentally wrong notion that signature and encryption are fully orthogonal. But generic generalizability can be ameliorated with a concerted, coordinated effort. As for S/MIME (specifically, working out how to embed CMS in MIME)... well, email and MIME make a good solution impossible from the outset, and S/MIME is probably the least bad you can do.

Encrypted email can never have a good solution simply because email is the poster child for "Why Postel's Law is a bad idea"

[woodruffw]

Completely agreed!

[tptacek]

I'm hanging back hoping 'woodruffw answers this so I don't have to. :)