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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#261

Post by Perceptes »

acchow wrote: post #256
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…

> meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport Can you elaborate on what you mean by this? If the message is encrypted (for example: PGP/GPG) why do I care whether the transport is secure or not?

It means that the end user is responsible for ensuring all data is encrypted, where it's easy to make a mistake and accidentally let something through unencrypted. Combined with this other bullet point:

> An unencrypted installed base that ensures encryption will be opt-in for the foreseeable future, meaning that users will routinely reveal plaintext accidentally by, for instance, quoting messages and forgetting to encrypt.

That spells disaster. This is in contrast to something like TLS, where a user with absolutely no technical understanding can visit a website with HTTPS without having to think about it at all (mixed content aside).

Re: Encrypted email is still a pain

#262

Post by Perceptes »

benevol wrote: post #177
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…

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.

Matrix will likely be on his list of suggestions soon, once end-to-end encryption support is out of beta and/or more mature. That is an open system.

Re: Encrypted email is still a pain

#263

Post by ivanstegic »

tptacek wrote: post #17
problems wrote: post #12

Earlier quoted context omitted.

> * Hundreds of millions of users that primarily access messages through browser clients that can't meaningfully implement crypto. Isn't protonmail pretty much a direct counter-example of this? They even have an extension you can use if you don't want their server to be trusted at all: https://chrome.google.com/webstore/detail/protonmail-checker... > * End user demands for things like search that can only be delivere…

No? Virtually nobody uses Protonmail. If the only thing between encrypted email and no encrypted email was a single provider that implemented PGP, we'd have had universal encrypted email in 1999. (I'm stipulating that anything Protonmail does actually, you know, works. I have no idea if it does. Why bother? Encrypted email isn't going anywhere. The track record on things like this is quite bad.)

> Virtually nobody uses Protonmail.

Please, cite a source. Or, show us with data.

Re: Encrypted email is still a pain

#264

Post by coldtea »

zeveb wrote: post #229
mikegerwitz wrote: post #201

Earlier quoted context omitted.

If you care about the physical identity of someone: web of trust. At some point, you'll have to ideally meet at least one person in the flesh to exchange keys and verify their identity. After that point, it's possible that others you are trying to communicate with might be within your web of trust. If not, you'll have to go through your keysigning procedure again. https://www.gnupg.org/gph/en/manual/x334.html Some or…

> After that point, it's possible that others you are trying to communicate with might be within your web of trust. The problem with the web of trust is that it simply doesn't work: the fact that I know you means nothing about whether I trust you to vouch for others. The fact that I trust you to vouch for employees of Acme Widgets means nothing about whether I trust you to vouch for members of the a political party.…

>The problem with the web of trust is that it simply doesn't work: the fact that I know you means nothing about whether I trust you to vouch for others.

Actually it means a lot. That's how trust works in the real world as well.

Re: Encrypted email is still a pain

#265

Post by atmosx »

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…

@tptacek is spot on actually: "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."

I don't know what the consensus among experts is because I'm definitely not one of them. However, the Podesta email scandal/hack/case take-away for me was that... if the most expensive, modern digitally-aware campaign ever made did not bother to use GnuPG for emails, it means that it is pretty much a dead-in-the-water tech.

Re: Encrypted email is still a pain

#266

Post by Kalium »

scotchmi_st wrote: post #43
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…

> why bother? Email is just one of dozens of messaging systems available to Internet users. Better to move sensitive conversations to things like Signal, WhatsApp, or Wire --- the double ratchet construction is designed specifically to make IM-like protocols secure even when conversations are sporadic and last months. This makes me sad. There's something profoundly democratising about the idea of running your own ema…

It is very hard to build a secure, distributed messaging system. It's even harder to run a secure one in a world where bad actors are known to exist in distributed, federated systems.

I understand why some might feel this is an overly cynical position to take. With that in mind, I would remind people that spam is a real problem in a real-life distributed, federated, open system.

Re: Encrypted email is still a pain

#267

Post by xeeeeeeeeeeenu »

threatofrain wrote: post #252
293984j29384 wrote: post #186

Earlier quoted context omitted.

A bold statement like that without a source just screams bullshit.

I think tptacek thinks in a way where he's giving you charity in an uneven discussion, so he's not obligated to go further; perhaps harsh, but his reputation warrants a little pause before simply saying "bullshit".

No, his reputation doesn't "warrant" anything. Internet discussions don't work this way.

If he claims something, he should be able to back it up with something else than his so-called "authority".

Re: Encrypted email is still a pain

#268

Post by jsprogrammer »

EGreg wrote: post #234
pera wrote: post #170

Earlier quoted context omitted.

> 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…

Why use PGP anymore when you can use Keybase and the next generation of key management? Instead of having one master key for your identity, the paradigm is changed: Identity is a set of claims "X on domain A is Y on domain B". That's it. "Domain" can refer to a server-based service such as reddit, or a client app on a device. Such proofs are easy: 1) For public identity on sites which don't support this scheme, X sim…

You still need to trust a set of claims under that scheme.

What if claims can be generated faster than you can verify them?

Re: Encrypted email is still a pain

#269

Post by Canada »

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…

SMS is federated, like everything else telecom. Just not as openly as SMTP.

Re: Encrypted email is still a pain

#270

Post by x0x0 »

cvwright wrote: post #199
Sunset wrote: post #188

Earlier quoted context omitted.

>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.

One idea: send them a signal (hi, this you?) then immediately dial their number and confirm.
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