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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#191

Post by m3rc »

pmlnr wrote: post #14
tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> But: why bother? Email is just one of dozens of messaging systems available to Internet users. No, it's not. It's the only widely available, decentralized system, with which you can send to anyone, if you know the address. None of the big ones is this open. XMPP tried to address this and failed; now Matrix is trying again.

By that logic shouldn't we try to encrypt SMS? Email as a protocol has huge security issues, and email as it is currently used honestly is NOT federated or decentralized.

Re: Encrypted email is still a pain

#192

Post by kyrra »

RyanZAG wrote: post #70
mrfregg wrote: post #61

Earlier quoted context omitted.

Forgive my ignorance, but what caused XMPP to fail? Simply the lack of uptake or is there some other reason?

Google's embrace-extend-extinguish destroyed XMPP. They made their chat system XMPP compatible for a short time which caused many people to swap to their solution. When they ended support, most users simply stopped using XMPP.

The rumor[0] was that Google killed XMPP because Microsoft was doing 1-way federation (Microsoft would not broadcast availability status or typing indicators).

[0] http://www.ucstrategies.com/unified-communications-strategie...

Re: Encrypted email is still a pain

#193

Post by mschuster91 »

tptacek wrote: post #22
pmlnr wrote: post #14

Earlier quoted context omitted.

> But: why bother? Email is just one of dozens of messaging systems available to Internet users. No, it's not. It's the only widely available, decentralized system, with which you can send to anyone, if you know the address. None of the big ones is this open. XMPP tried to address this and failed; now Matrix is trying again.

WhatsApp has over a billion users. There are big places where its market share exceeds that of SMS --- another big centralized service that has a userbase comparable to that of email. My conclusion is that the people who care about "decentralized" systems are a rounding error. I care about non-technologists managing to send asynchronous messages to each other that are well-encrypted by default. That's a solved proble…

> There are big places where its market share exceeds that of SMS

The "market share" of SMS is the entire world. SMS works with anything from a $15 Shenzen dumb-phone to a $1k iPhone 7+. Not to mention that unlike WhatsApp, which is forbidden to do business with countries like Iran (due to US export regulations), SMSing works with any country in the world except North Korea.

Re: Encrypted email is still a pain

#194

Post by m3rc »

Certhas wrote: post #140
lmm wrote: post #89

Earlier quoted context omitted.

> In modern messaging protocols, they don't have to care about encryption. The protocols are designed to reliably encrypt messages without user intervention, and security isn't "opt-in". Sounds good. Doesn't sound worth giving up decentralisation for. Doesn't even seem like something we'd need to give up OpenPGP to get - if client design were equal (and it isn't at the moment, but I see no reason it can't be) I'd far…

What's the benefit of decentralization? Not being snarky, I just don't really see it. What does a decentralized PGP email have that I don't have with my Signal Messenger? Also, given how PGP works I fail to see how you can claim that you can achieve comparable client design/ease of use/UX to Signal. At the very least it appears evident to me that the problem is much much harder than Signal (and it should be, Signal w…

Harder to prevent access to, harder to wire-tap. As other people pointed out WhatsApp has been blocked in countries before. Not to mention that with WhatsApp having a central location all messages are routed through we really don't have any guarantee that there isn't a compromised actor in there intercepting everything. Even if WhatsApp's crytpo is as flawless in implementation as we'd like FB still has access to all that metadata.

Re: Encrypted email is still a pain

#195

Post by eatbitseveryday »

tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> Better to move sensitive conversations to things like Signal, WhatsApp, or Wire

Will corporations adopt these platforms? You cannot share files easily, create threaded conversations, etc. More-over, one must register a phone number, and rely on the centralization of the provider of the service.

For some uses, emails serve as a record of communication, and to establish a public history of conversation (e.g., open-source development mailing lists). However, for these cases, encryption isn't used.

Re: Encrypted email is still a pain

#196

Post by NoGravitas »

__jal wrote: post #164
Certhas wrote: post #140

Earlier quoted context omitted.

What's the benefit of decentralization? Not being snarky, I just don't really see it. What does a decentralized PGP email have that I don't have with my Signal Messenger? Also, given how PGP works I fail to see how you can claim that you can achieve comparable client design/ease of use/UX to Signal. At the very least it appears evident to me that the problem is much much harder than Signal (and it should be, Signal w…

> What's the benefit of decentralization? No single point at which to apply judicial- and/or rubber-hose cryptography is the big one. I do agree that the problem-space of attempting to make a reasonable UI for GPG has been explored for a long time with no useful results. I'd love someone to prove me wrong, but it seems like that's a hopeless endeavor. It is worth asking why, though. I'm not a UI person, so apply appr…

I don't think the real problem with OpenPGP is the UI issues. OpenKeychain and K9-Mail together provide a not terrible UI for OpenPGP, and if someone wanted to more tightly integrate them with each other,the UI could probably be improved further.

But PGP-over-SMTP would still leak important metadata, and you would still have problems with forward secrecy and key revocation.

Matrix looks like a much better decentralized solution to build a new email infrastructure on. But there are still metadata leakage issues with federation, and there need to be some standards and an example implementation for email-over-matrix.

Re: Encrypted email is still a pain

#197

Post by m3rc »

Certhas wrote: post #176
lmm wrote: post #172

Earlier quoted context omitted.

> What's the benefit of decentralization? Not being snarky, I just don't really see it. What does a decentralized PGP email have that I don't have with my Signal Messenger? It's a lot harder to block. You can have anyone run a mail server on any port (SSLed if necessary), which means you can use it for secure communications inside any "great firewall" (like that of China or Kazakhstan), or even in a country/region th…

https://whispersystems.org/blog/the-ecosystem-is-moving/ One of the explicit protocol level trade offs is federation: > One of the controversial things we did with Signal early on was to build it as an unfederated service. Nothing about any of the protocols we've developed requires centralization; it's entirely possible to build a federated Signal Protocol based messenger, but I no longer believe that it is possible…

Signal making choices for ease of evangelizing it doesn't condemn the entire idea any more than poor implementations of secure email means we should totally give up on it

Re: Encrypted email is still a pain

#198

Post by Freak_NL »

m3rc wrote: post #191
pmlnr wrote: post #14

Earlier quoted context omitted.

> But: why bother? Email is just one of dozens of messaging systems available to Internet users. No, it's not. It's the only widely available, decentralized system, with which you can send to anyone, if you know the address. None of the big ones is this open. XMPP tried to address this and failed; now Matrix is trying again.

By that logic shouldn't we try to encrypt SMS? Email as a protocol has huge security issues, and email as it is currently used honestly is NOT federated or decentralized.

For personal use email is rarely self-hosted, but corporations, governments, and organisations often run their own email infrastructure. That effectively makes email a decentralized federated system.

You might argue how a lot of email is either send to or send from Google, Apple, or Microsoft services, and that is thus somewhat centralized, but isn't that stretching the definition?

Re: Encrypted email is still a pain

#199

Post by cvwright »

Sunset wrote: post #188
lallysingh wrote: post #178

Earlier quoted context omitted.

The hardest problem, IMHO, has been key management. How do you get+trust the other's key? I think a combination of keybase + a useful client can help, but the reasons listed in parent are pretty convincing.

>How do you get+trust the other's key? Snail mail + several other out of band methods. Or you can exchange a one time pad, physically.

This also raises the question: With a walled garden like Signal/Wire/etc, how do you get+trust the other's key?

Their convenience comes at a cost.

Re: Encrypted email is still a pain

#200

Post by joecool1029 »

corv wrote: post #187
joecool1029 wrote: post #179

Earlier quoted context omitted.

> No, it's not. It's the only widely available, decentralized system, with which you can send to anyone, if you know the address. None of the big ones is this open. SS7 is internet connected and federated and it's arguably as big as email. > XMPP tried to address this and failed; now Matrix is trying again. Oh, agreed on XMPP. Encryption was a very much after the fact addition to it though. I haven't heard about Matr…

http://matrix.org/ is a promising decentralized communications protocol. The popular https://riot.im is built on top.

> The popular https://riot.im is built on top.

Thanks, so it's basically a opensource and federated slack?

How does this solve the email encryption use case? (longer form text not requiring presence)

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