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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#171
post #99
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 Really? Come on! WhatsApp is owned by a company whose business is done by retrieving all the information it can from users and by tracking their behaviors.

WhatsApp doesn't just support¹ Signal's end-to-end encryption, it enables it by default for everyone with no option to turn it off. It successfully prevented my government² from decrypting user messages even with court orders.

It's a major improvement over whatever bolted-on security email has.

¹ https://whispersystems.org/blog/whatsapp-complete/

² https://www.forbes.com/sites/parmyolson/2016/05/03/whatsapp-...

Re: Encrypted email is still a pain

#172
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…

> 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 that's been cut off from the Internet (which we've seen happen for various amounts of time in Syria, Crimea, Turkey...). WhatsApp/Signal have a very limited version of this by getting makers of popular HTTPS services to work with them, but those services are subject to their own commercial pressures (all the big names have been known to collaborate with e.g. the Chinese authorities in the past) and attackers always have the option of just blocking those services outright.

It rules out a whole class of attacks involving compromising the central servers and tricking the client into redoing an initial exchange. If the Signal client is implemented correctly this shouldn't be an issue, but it's an extra attack surface that simply doesn't exist for OpenPGP.

Also compared to Signal et al it's more practical (though still difficult) to use pseudonymously, because a pseudonymous email address is eaiser than a pseudonymous phone number. Signal advocates talk about having deniability because your messages aren't provably signed by you, but I don't think that advantage exists in any reasonable threat model - if we're worried about a state adversary hunting down everyone who corresponded with dissident x, they'll find it easier to track down a phone number than an email address, and once they've tracked down one of x's correspondents (i.e. someone who has a phone with a number that exchanged messages with x) they're not going to be bothered by the fact that they don't have signed mathematical proof that this is the same person who corresponded with x.

> Signal was designed from the ground up with UX in mind, and made several important trade offs for it

Such as? At the protocol level I mean.

Re: Encrypted email is still a pain

#173
post #70

Earlier quoted context omitted.

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.

Did you also notice that Google's messaging system pretty much died out around that point in favor of Skype and similar? I used to see people mention GTalk all the time, but I haven't seen anything similar in years. No one has mentioned G+ or Allo. That decision by Google may have been the thing that killed its user base.

No, it turned into Hangouts, which is alive and kicking, specially for companies using Google Apps.

Re: Encrypted email is still a pain

#174

Earlier quoted context omitted.

Did you also notice that Google's messaging system pretty much died out around that point in favor of Skype and similar? I used to see people mention GTalk all the time, but I haven't seen anything similar in years. No one has mentioned G+ or Allo. That decision by Google may have been the thing that killed its user base.

Hangouts (which I think GTalk turned into) still has some usage - certainly as a quick video conf call solution, and somewhat for text messaging. It definitely doesn't seem to have much of a future though since Google released a bunch of other competing chat applications.

It's unfortunate because Hangouts is still really awesome. It works really well for video chat (including group chat), but more importantly it works great with multiple devices. I can get a message on my phone, laptop or PC, and reply anywhere, with the conversation and notifications synchronized. I nearly always have my phone with me, but it's really nice to be able to just send someone a link from my PC, for example.

It looks like Telegram has multi-device support, but then this kind of thing scares me:

> Q: How are you going to make money out of this?

> We believe in fast and secure messaging that is also 100% free.

> Pavel Durov, who shares our vision, supplied Telegram with a generous donation, so we have quite enough money for the time being. If Telegram runs out, we will introduce non-essential paid options to support the infrastructure and finance developer salaries. But making profits will never be a goal for Telegram.

That's not very compelling in terms of investing my effort to switch.

Re: Encrypted email is still a pain

#175
post #164

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…

> the problem-space of attempting to make a reasonable UI for GPG has been explored for a long time with no useful results

Has it? Have we ever had even e.g. 2 reasonably skilled design professionals spend a year trying? That would, I suspect, be much less effort than has gone into Signal et al. But still beyond the resources of volunteer-only FOSS, unfortunately.

Re: Encrypted email is still a pain

#176
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? 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? 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 to build a competitive federated messenger at all.

Re: Encrypted email is still a pain

#177
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…

This sounds like a "drop your pants and surrender already" post.

You could add at least some constructive advice or strategy. And using...

a) closed platforms (silos) that

b) run on closed-source code that's

c) produced by companies that are PRISM partners

...is not in the interest of anybody who values real privacy and requires a solid basis for freedom of speech and democracy.

Re: Encrypted email is still a pain

#178
post #170
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…

> The emerging consensus among experts "conseunsus"? a few blog posts about some bad user experience with GnuPG / the PGP ecosystem is, at best, just an (re)emerging topic on HN, not the end of email encryption. OpenPGP implementations may not be the easiest encryption software out there (its usability issues have been discussed for two decades now) but that's simply because PGP was not designed to be used by the lai…

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.

Re: Encrypted email is still a pain

#179
post #14
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.

> 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 Matrix and plugging in 'matrix encrypted email' into search gets 0 relevant results on DDG and is bottom of the page for Google. Maybe the ranking sucks cause the page takes 20s to load the JS shit and it has zero content aside from a bouncing fucking shitball above the fold.

Re: Encrypted email is still a pain

#180
This is one of the reasons that disrupting email is one of the most popular bad ventures. It's great 1980's tech. Email is a false vacuum in the field of solutions for communication, a local minimum. We can't improve on it any futher - every direction along the gradient of solutions is a worse solution.

IM is doing a good job at locating a new local minimum right now.

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