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.

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woodruffw a day ago | parent [-]

> but i suppose that swapping out PGP for something entirely different should technically be possible.

That would probably be good, but email is still a terrible substrate for secure messaging. Clear metadata is security poison; you want as little of it revealed to participant servers as possible.

> they did develop a peer to peer protocol with forward security for real-time messages that sidesteps SMTP entirely.

That’s great, but in that case: what’s the value proposition relative to Signal or even Matrix?

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em-bee 21 hours ago | parent [-]

the peer to peer protocol at this point is only for realtime communication at which both parties have to be present. like IRC, those messages are not saved. it does not replace regular messaging which is stored. i was merely trying to point out that the developers are capable of thinking outside of the box that they started from and that deltachat may develop in a different direction. as someone else stated, deltachat's value is that it is able to reuse existing infrastructure and does not require (but allow) a new set of servers to be able to work.

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woodruffw 19 hours ago | parent [-]

> i was merely trying to point out that the developers are capable of thinking outside of the box that they started from and that deltachat may develop in a different direction.

I mean this kindly: I wish they would think a little bit more inside the box, and converge onto a proven design.

(It’s worth noting that your “existing infrastructure” argument is exactly why Signal uses phone numbers. Using existing infrastructure is a great idea, so long as it doesn’t compromise the security expectations any reasonable user has. That isn’t currently true for Delta Chat.)

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em-bee 4 hours ago | parent [-]

exactly why Signal uses phone numbers

the reason may be the same, but the effect is entirely different. until recently signal did not allow hiding the phone number, failing my privacy expectations. a public phone number is something entirely different than a public email address. signal is also centralized with its own servers. deltachat works completely without dedicated servers. and emails easily allow multiple accounts.

and what are reasonable security expectations? what you and i consider reasonable does not at all match what the general population expects. for most people sending encrypted emails would already be a win. (autocrypt also works with regular email clients, not just deltachat)

the goal here is to raise the general use of encryption in messages. if that is not sufficient then deltachat is not the right tool. but i have friends on telegram and whatsapp. getting them to use deltachat would be an improvement.

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woodruffw 3 hours ago | parent [-]

Centralization is not a security property in the context of E2EE. You can want decentralization (I often do), but it’s essentially an ideological demand rather than a security preference when the server provably has no access to your messages or metadata.

> and what are reasonable security expectations?

End-to-end encryption that the user can’t accidentally downgrade from and that doesn’t spray valuable metadata across the Internet. That’s table stakes; I’m not interested in lowering my standards below that.

> for most people sending encrypted emails would already be a win.

I don’t think this is even remotely true. I think the average person doesn’t know what an encrypted email is. We’re now in at least the third decade of encrypted email techniques, and adoption outside of corporate S/MIME (another can of worms) is marginal.

There’s almost too much to even say here; it’s a disservice to even accept the implicit assumption that users would use encrypted email correctly if they could be made to: the single most common breakage point for all of this stuff is still people replying or forwarding previously encrypted messages in the clear!

> the goal here is to raise the general use of encryption in messages.

No. The goal is security. “General use of encryption” goes back to putting ideology before security. The goal is to actually put users in a position where adversaries struggle to collect the kinds of data and metadata that would allow them to harm people. The US famously kills people based on metadata[1], and we’re the “strict” ones in terms of evidentiary standards.

[1]: https://www.nybooks.com/online/2014/05/10/we-kill-people-bas...

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em-bee 3 hours ago | parent [-]

Centralization is not a security property

true, i wasn't thinking about security here but reuse of infrastructure. signal doesn't reuse infrastructure because it needs its own servers.

End-to-end encryption that the user can’t accidentally downgrade from

that's a fair point.

that doesn’t spray valuable metadata across the Internet

i find that a gross exaggeration. yes. metadata can be read by every server the mail passes through. but in practice most mails are only touching the sending and the receiving mail server. if both of those servers are in control of the sender and recipient and the connection between them is encrypted then the metadata remains private.

also, where i use deltachat, the alternative is to use email.

I think the average person doesn’t know what an encrypted email is

which is why we need more encryption by default.

adoption outside of corporate S/MIME is marginal.

because it is to hard to use. deltachat makes it easy to use. next possible step: delta mail. a more traditional mail client that makes encryption as easy as deltachat does.

The goal is to actually put users in a position where adversaries struggle to collect the kinds of data and metadata that would allow them to harm people

there is a long road to get to that. more encryption is just one step, but a necessary one. i agree with you, but the goal can't be reached if we don't work on multiple fronts. one of those is helping people to learn about encryption and privacy, which only happens by slowly getting them to use better tools and by improving those tools.

rejecting deltachat is rejecting something that improves the current state for something better that is not obtainable by some. sometimes that makes sense, especially if the solution promises more than it holds. and deltachat would fall into this if it were to promise complete privacy. but i don't think it does that.

i have friends who outright refuse to sign up to a new service. but deltachat is ok because they can use their existing email for it. technically that sounds the same as saying that with signal you can reuse your existing phonenumber, but people already have much higher privacy expectations to sharing their phone number, and also deltachat doesn't share your email address except with recipients so it really isn't the same thing.

	▲	woodruffw 2 hours ago \| parent [-]
		> if both of those servers are in control of the sender and recipient and the connection between them is encrypted then the metadata remains private. Why are we entertaining this hypothetical? It isn’t true in practice; the average user doesn’t control their mail server. The average user is using Gmail or Outlook, where their metadata is a single subpoena away. And again, it just isn’t true: you need not just control over the server but also strict transport security for this property. This is not widely true of mail servers on the Internet. > rejecting deltachat is rejecting something that improves the current state for something better that is not obtainable by some. I don’t agree. I think the average user has multiple high-quality E2EE messaging technologies available to them, and that Delta Chat effectively muddies the water by providing a worse security posture with the trappings of a familiar-but-unsecurable ecosystem (email). (I also don’t know why people think Signal shares your phone number with people other than recipients. To my knowledge, that has never been the default and presumably never will be, even with their private contact discovery protocol.)