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It's my understanding that most of these secure messaging system relay via servers speaking https - and their distinctive feature is that the clients are distri

by e12e 9y ago

It's my understanding that most of these secure messaging system relay via servers speaking https - and their distinctive feature is that the clients are distributed as self-contained apps, that wrap the complexity, and label "signal-protocol over https rpc" as just "signal" (similar for WhatsApp etc). Why is it hopeless to do the same for email? Take a sane protocol subset, add a convention protocol for encryption, and ship it as "secure email"? It is a tautology that a "secure mail app" that allows "traditional email interop" cannot make strong privacy guarantees, just like when using WhatsApp you give up federation and networking-as-a-utility (you're completely beholden to a provider that you don't even have a proper contract with, let alone the opportunity to seamlessly move providers / self-host / federate while maintaining global addressing and data portability). I think that's part of the disconnect in the discussion - wrapping a sane protocol selection in an opaque app along with a saas/paas silo that limits addressing, routing and federation is OK for some arbitrary subset of not-by-themselves secure protocols, but any suggestion that reusing elements of email is dismissed as "can't be done" (or "can't be done, because webmail", while "can't be done because messenger.com" seems absent). We've already done meta-data wrapping for email, with one, perhaps flawed approach: https://en.m.wikipedia.org/wiki/Mixmaster_anonymous_remailer https://en.m.wikipedia.org/wiki/Mixmaster_anonymous_remailer

tptacek 9y ago
Secure messengers might use TLS (though probably not HTTPS) to connect to servers, but messages themselves are independently encrypted: they don't rely on TLS for message encryption.
- e12e 9y ago
  Right. And gpg messages are also independently encrypted, although subject isn't scrubbed by default, and some routing information leaks by default (although eg Mixmasters exist as one approach for mitigating the latter to a certain extent. All system will need to have some routing information. Come to think of it, gpg+usenet might be "better" example of "old tech" secure messaging). Ed: i suppose the question.becomes if new systems rely on tls to help obscure meta-data or not; like what mail+gpg does.

by e12e 9y ago

tptacek 9y ago

Secure messengers might use TLS (though probably not HTTPS) to connect to servers, but messages themselves are independently encrypted: they don't rely on TLS for message encryption.

e12e 9y ago
Right. And gpg messages are also independently encrypted, although subject isn't scrubbed by default, and some routing information leaks by default (although eg Mixmasters exist as one approach for mitigating the latter to a certain extent. All system will need to have some routing information. Come to think of it, gpg+usenet might be "better" example of "old tech" secure messaging). Ed: i suppose the question.becomes if new systems rely on tls to help obscure meta-data or not; like what mail+gpg does.