As a side note, despite its popularity, Texas hold'em is just one type of poker game. In most poker games (5 draw, 7 stud, etc..) you ante every hand.

GPG is gnu privacy guard, it's an open source implementation of the same ideas that are PGP (pretty good privacy).

Specifically we're supposed to call it OpenPGP these days

OpenPGP is a message format standard, not an architecture standard. Since they are doing a instant messaging thing, there is no particular reason they couldn't do forward secrecy. They could even do a hash ratchet and call the result a double ratchet if they really wanted to. It would probably be more reasonable to do something a bit less obsessive and just make it so that the user can more securely delete their messages in the face of device compromise in an instant messaging environment.

PGP isn’t architecturally well-equipped to provide forward secrecy

i have no insight into the development, but i suppose that swapping out PGP for something entirely different should technically be possible.

they did develop a peer to peer protocol with forward security for real-time messages that sidesteps SMTP entirely. seems a bit wierd given the premise, but the devs are at least not limiting themselves to SMTP and PGP.

This conversation is important, and weighing these aspects against each other is critical in order to form better opinions. We clearly both agree there are subtle and counter-intuitive effects at play. I don't think there's anything wrong with debating them, and I'm happy to be convinced otherwise.

> Unless your messenger is at pains to make sure people don't use it in life-or-death situations [...] the exact opposite thing is true

Right, this is the false-sense-of-security effect. It exists and it's real. But there are more aspects that weigh in.

> People always have a third option: not sending the message electronically.

I challenge this assumption. In reality the effect is not about what they can do if they listen to the advice of Bruce Schneier, but what they will do. Navel-gazing on security and throwing your hands up if people don't act "the way they should" is what's really irresponsible, imo. I.e. if your contacts are not physically close, they won't (or even can't) schedule a flight to send a message. They'll generally use what's socially convenient, even if they're discussing something like abortion in an oppressive state. If you're lucky non-techies will say "Hey, maybe we should try that app Signal, I heard it's more secure". That's as good of a win as it gets.

The counter-example would be going around saying Signal is worthless because they collect phone numbers, they don't enforce public key validation, and they don't use onion routing to protect your social graph. I don't think we disagree about how ridiculous that would be, even if we disagree on which aspects are most important.

Basically, if set the weight of all security properties to ∞, you will get something that's so wildly inconvenient that nobody would use it. Even PGP that's relatively easy to use was at its peak about as popular as starting a yak farm.

> famously minuscule metadata

Famously minuscule? They demand a phone number, which blows up any possible anonymity story.

> What parts of this do you think are missing from Signal?

The social graph isn’t e2ee in any app that works because the server needs to route the message. And the social graph is metadata.

Signal is notably not proprietary. And email is de-facto owned by a small handful of service providers.

Telling Joe Shmoe that he should run his own email infrastructure instead of using literally anything actually built for E2EE is an ideological argument, not one grounded in Joe’s message security expectations.

All of which is true and praiseworthy.-

Sadly, as with many things, Gmail effectively controls it de facto, nowadays ...

> Which are you leaning towards to and why?

Heavily sandboxed SimpleX that's firewalled to block any non-Tor traffic. Chose this one because it allows for offline message sending/receiving, despite privacy implications, and because it has clients people will actually use.

Cwtch doesn't let you send messages when the recipient is offline by virtue of how it works, which is more secure, but inconvenient.

When evaluating Cwtch, I think I read somewhere it might send identifying metadata to your recipient, or something similar, but I might just be making that up. I'll have to look up what I was reading.

> > identify that and when a user is using SimpleX.

> Does this apply to Cwtch?

With Cwtch you're running two hidden services, one on either end of the chat, and that happens over Tor with no middleman service, so no. A passive network observer can tell when you're connecting to Tor, but you can attempt to obfuscate that with transports.