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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#391

Post by throwanem »

e12e wrote: post #342
m3rc wrote: post #189

Earlier quoted context omitted.

There are federated options for messengers, the fact that the current darlings aren't is not a mark against the option itself. Riot exists. Can you find a security expert RECOMMENDING email? That would be a better example of how it's not a consensus, like you claim.

As far as I can tell, encrypted email is still how you reach out to CERT, security teams at distros such as Ree Hat, Debian and so on? These people might not be crypto experts, but hopefully many of them are security experts. Gpg is also how most mailing list communication is (clear-)signed - and that coupled with public archives does give a way to verify that the person that controls the key that signed release note…

> every blank staring IMAP-client writing developer keep saying that there are terrible horrors laying in ambush for the unwary

Oh, my, yes. Lasciate ogni speranza...

Re: Encrypted email is still a pain

#392

Post by mikegerwitz »

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.…

If you don't trust that individual to vouch for others then they are treated differently in your web of trust: set their trust level to "none".

If you refuse to place trust in anyone, then no, the web of trust will not work for you. But it works for many others; it doesn't make it broken. The purpose of key signing is to verify that a person is legitimately who they claim to be---_that_ is what you are trusting in your web of trust: that someone has verified their identity in a means consistent with accepted protocols.

If enough people say "this person is who they say they are" by signing that person's they, then you decrease the odds that the person is a fraud.

Re: Encrypted email is still a pain

#393

Post by [deleted] »

b2600 wrote: post #367
JustSomeNobody wrote: post #148

Earlier quoted context omitted.

Google, Apple, Facebook, WhatsApp. Everyone[0] is using one of these. None are XMPP or compatible with XMPP. [0] I don't technically mean the entire planet.

Curious why you tossed Apple in there. In worldwide usage it's a fraction compared to the other three. (I feel compelled to state I use an iPhone in order to avoid this comment being interpreted incorrectly).

[deleted]

Re: Encrypted email is still a pain

#394

Post by synchronise »

girvo wrote: post #365
dredmorbius wrote: post #362

Earlier quoted context omitted.

Wait: which one is that?

Singal, nee TextSecure, I'd assume. Edit: Crap, I mean WhatsApp, which _uses_ Signal's protocol now.

Does WhatsApp have reproducible builds yet? Do we know that the app isn't storing the keys somewhere else?

Re: Encrypted email is still a pain

#395

Post by whyagaindavid »

I want email to stay at least for work related. Imagine your employer shifts to WhatsApp or signal. Asks you to code shady stuff. Even if you resign, there is no proof your manager knew it if your official mobile phone was wiped. Think about harassment from senior managers. All these go undocumented. This is why I prefer my email from and to every one in office to be plain text. No PGP. I am German; do not care Hillary or Trump - but if Hillary had used signal. May be things would be different!

Re: Encrypted email is still a pain

#396

Post by tzs »

WalterBright wrote: post #285
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…

The way to do it is to have it be a standard feature of the email client. Your client, if it supports it, generates the public/private key automatically. Every time it sends an email, it includes the public key. Every time it receives an email, it stores the received public key if there is one. Every time an email is sent, it encrypts it automatically if the address book has the public key. Over time, it will work it…

There was a company that offered a product for Windows 95/98 users around 2000 that did that, except it worked with existing email clients instead of requiring new ones. It worked reasonably well, as long as the user understood the limitations such as the metadata issue.

There was no common extension interface for the major email clients (and many didn't have any extension support), so their biggest technical challenge was finding a reasonable way to hook in between the user's email client and the network.

Their first approach was to have their program run as a daemon that implemented SMTP and POP3, and the email client's proxy settings were changed to use the daemon as a proxy. Their setup program recognized the top email clients and know how to change their proxy settings. For other clients the user might have to manually change their proxy settings.

Later they switched to using the LSP interface to hook into the network stack to intercept and modify email regardless of what email client was being used.

Re: Encrypted email is still a pain

#397

Post by ryanmarsh »

joecool1029 wrote: post #179
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.

> 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…

What is SS7?

Re: Encrypted email is still a pain

#398

Post by cvwright »

maxerickson wrote: post #311
cvwright wrote: post #300

Earlier quoted context omitted.

Yup, and I've done these. But you can do similar things with PGP public keys, too.

I don't understand. You've verified a Signal key but still felt the need to ask the question With a walled garden like Signal/Wire/etc, how do you get+trust the other's key? What cost were you talking about then?

Sorry if my earlier comment came off as rude. I was just trying to say that the walled gardens aren't really that much better than plain old PGP, and in practice they tend to lull people into a false sense of security.

I think too many people are way too trusting of shiny new apps with a pretty UI. If you don't do the extra work of verifying the key, you're effectively letting the service provider act as your one and only CA.

If you can verify a Signal key fingerprint, you can verify a PGP public key fingerprint.

Re: Encrypted email is still a pain

#399

Post by Arathorn »

rhblake wrote: post #323
Arathorn wrote: post #239

Earlier quoted context omitted.

Just to clarify: identity servers are strictly optional and are used just for mapping 3rd party IDs (3PIDs) such as phone numbers and email addresses to matrix IDs so you can be discovered or discover other users by 3PID. They are only centralised atm because we haven't really started to attack the problem of decentralising them. What we really need is a decentralised equivalent of Keybase, but nobody has really buil…

Re: metadata: I really like Riot/Matrix and have convinced a bunch of formerly non-IRC people to start using IRC through Matrix (the great free IRC bouncer in the sky!). However, a couple of things that bother me: - The fact that it appears to be impossible to disable typing notifications ("X is typing...") and read receipts. This can change the nature of a conversation and really should be optional. Coming from IRC,…

These are https://github.com/vector-im/riot-web/issue/3220 and https://github.com/vector-im/riot-web/issue/2295 respectively. Agreed that the info currently leaked in device info sucks - please vote on the issues to get them bumped up the todo list!

Re: Encrypted email is still a pain

#400

Post by chimeracoder »

synchronise wrote: post #394
girvo wrote: post #365

Earlier quoted context omitted.

Singal, nee TextSecure, I'd assume. Edit: Crap, I mean WhatsApp, which _uses_ Signal's protocol now.

Does WhatsApp have reproducible builds yet? Do we know that the app isn't storing the keys somewhere else?

> Does WhatsApp have reproducible builds yet?

WhatsApp isn't even open source, so no, it doesn't have reproducible builds. (Signal is open source and does have reproducible builds).

> Do we know that the app isn't storing the keys somewhere else?

No, but WhatsApp is still strictly better than either email or SMS. Even if you don't trust Facebook, that still only leaves three parties that can compromise the integrity of messages (you, the recipient, and Facebook), as opposed to the uncountable number of parties that can passively observe email or SMS in transit.

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