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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#431

Post by dTal »

dtornabene wrote: post #368
dredmorbius wrote: post #363

Earlier quoted context omitted.

Your comment is its own best response to itself.

except that its ....not? You don't have to treat the snowden leaks as gospel, you know that right?

Even the government stopped denying their truth, especially after the drip feed of info caught them in baldface lies on several occasions. Also, if the info wasn't genuine, why would they be so upset and calling Snowden a "traitor" etc?

Additionally, this wasn't even the first time any of us had heard about this sort of thing. Ever heard of Room 641A? The Snowden leaks aren't exactly implausible or unprecedented.

I don't know if you are genuinely unsure of their veracity or just making a rhetorical point, but it's not a point of contention in any serious debate forum I know of, even among intelligence community sympathizers.

Re: Encrypted email is still a pain

#432

Post by tptacek »

dTal wrote: post #430
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…

>emerging consensus among experts Citation needed. >at best you're attempting to tunnel encrypted messaging over an unencrypted transport Like every encryption scheme ever. >A protocol that leaks metadata They all do? At best you get to choose which provider sees it, and even then timing attacks usually make short work. >browser clients that can't meaningfully implement crypto >search that can only be delivered effic…

This is incomprehensible to me. "Timing attacks" don't make short work of the equivalent of email metadata. Different systems reveal different amounts of metadata.

Re: Encrypted email is still a pain

#433

Post by openplatypus »

legulere wrote: post #127

I do not get why everyone thinks that encrypted email is GPG. S/MIME is supported by almost all email clients. S/MIME is far less of a pain (but still some pain and could be improved). It has a model of how to verify that keys belong to the right person, that actually works in practice in contrast to GPG where you basically have to verify keys by hand (adversarial CAs are a problem, but probably only for a tiny amoun…

Speaking of which, any decent S/MIME issuer/CA out there? I used StartSSL but there is some stink around them.

Re: Encrypted email is still a pain

#434

Post by jhasse »

tom-jh wrote: post #226
chippy wrote: post #222

Earlier quoted context omitted.

theres something screwy with the images on the testimonials part of the page: http://i.imgur.com/RFoqpKwl.png

(edit: it's fixed now) First time I see it like that, I assume one of your plugins is blocking it (direct links to google profiles). I'll store the images & serve them directly. Thanks!

Still not fixed for me. (Firefox with Ublock Origin)

Re: Encrypted email is still a pain

#435

Post by Akkuma »

tptacek wrote: post #34
patrickread wrote: post #10

If you're OK with using a third-party and would rather stick to GUI's, Virtru is a very easy solution for email encryption: https://www.virtru.com/

Where by "email encryption" we mean "mail people a link to a service they can register with and then upload messages and file to, so that SMTP is used only to relay links to messages, not the messages themselves, and email is encrypted by dint of TLS connections". That's what most F-500 companies do to solve this problem. It's a more viable approach than direct encryption of PGP. Normal people --- and eventually the…

This is a bit of a stretch of what the service does. You don't need to "register" to read messages. It OAuths you if you don't use the extension. People using the extension register through OAuth as well.

The email is encrypted before it is sent anywhere using AES 256 (GCM when available moving forward).

WhatsApp doesn't deal with email or file attachments as far as I knew to the same degree as something like gmail where we can handle ~150MB files and they handle ~30MB. I doubt most of these big companies want to migrate emails away from Outlook/Gmail and force all their external correspondence to be done via WhatsApp.

There's also rollout starting for support of customer managed keys and a bunch of things WhatsApp will probably take a long time to do, if ever, due to their consumer focus.

Disclosure: Work at Virtru

Re: Encrypted email is still a pain

#436

Post by confounded »

newscracker wrote: post #409
confounded wrote: post #364

Earlier quoted context omitted.

I got a group of about 30 non-technies using Signal, not because they knew what what perfect forward secrecy is, but because they grew vaguely suspicious of the motivations of governments and Facebook, and people/Google-results they trusted were positive. The details don't matter to ordinary people, but our approval matters much more than you think. I have very high hopes for Matrix.org.

I think your group of people would be highly disappointed whenever each person moves to a new device and finds that they have essentially "lost" all old messages and have to re-join groups afresh. > The details don't matter to ordinary people, but our approval matters much more than you think. I have very high hopes for Matrix.org. I agree on this part completely, and I try to introduce better tools to others too. Bu…

You're right, losing messages is a bad experience for most people.

Re: Encrypted email is still a pain

#437

Post by tommorris »

NoGravitas wrote: post #422
tommorris wrote: post #415

Earlier quoted context omitted.

> Better to move sensitive conversations to things like Signal, WhatsApp, or Wire Just download an app that requires you to register with your phone number and then hand out your phone number to anyone you want to chat to. I mean, all the NSA-proof crypto is fantastic, but they didn't exactly test it with anyone who has had to worry about less theoretical non-state actors like, oh, jealous exes, abusive partners, cre…

Yes, I find this a worrisome feature. I understand why they make this tradeoff -- it makes onboarding trivial. And it lets them piggyback contact discovery off of people's existing address books. But the downsides are very significant and rarely acknowledged.

I'm not sure it does make onboarding trivial. How do I join WhatsApp/Signal/Telegram with an iPad or iPod Touch? A laptop? A handheld gaming console like a PlayStation Vita? I can't sign up for any of these services without a phone and a phone number. Sorry, my phone number is a legacy communication layer that should just be replaced by the Internet.

When I went to Brazil last year, I switched the SIM in my phone from a UK one to a Brazilian pay-as-you-go SIM. WhatsApp said "oh, you've changed SIM, do you still want to use your existing (UK) number?" I guess that's okay behaviour. Does Signal do this? Does Telegram do this? I don't know. I have to keep track of what goes on when I change my SIM. That's a layer violation. The network I use to access the Internet shouldn't affect the behaviour of my messaging app. If I'm chatting to my friends, it shouldn't matter whether I have a UK SIM, a Brazilian SIM or no SIM at all.

What if I move from the UK to Brazil permanently and get a long-term mobile contract? Shall I still use my UK number for WhatsApp/Signal/Telegram or should I use a Brazilian one? Will I lose my contacts? Will they stop being able to talk to me because my number has changed? I don't know. That's pointless administrative overhead.

What if I let my pay-as-you-go number go stale? If you don't make a call or text for six months or so, the mobile network may disconnect your number. At some point, they'll reassign that number. Can that person now access my WhatsApp/Signal/Telegram? Okay, well, maybe we put a secondary password on it like Telegram to stop the account getting hacked if I lose access to the mobile number. Now the person who inherits my phone number can't set up their own Telegram account because I'm already "squatting" the old number.

This is ridiculous to me. It's like an Internet without DNS, where we have to manually keep track of each other's IP addresses. Nasty legacy phone network shit. Don't need it, don't want to deal with it.

Re: Encrypted email is still a pain

#438

Post by NoGravitas »

tommorris wrote: post #437
NoGravitas wrote: post #422

Earlier quoted context omitted.

Yes, I find this a worrisome feature. I understand why they make this tradeoff -- it makes onboarding trivial. And it lets them piggyback contact discovery off of people's existing address books. But the downsides are very significant and rarely acknowledged.

I'm not sure it does make onboarding trivial. How do I join WhatsApp/Signal/Telegram with an iPad or iPod Touch? A laptop? A handheld gaming console like a PlayStation Vita? I can't sign up for any of these services without a phone and a phone number. Sorry, my phone number is a legacy communication layer that should just be replaced by the Internet. When I went to Brazil last year, I switched the SIM in my phone fro…

Yeah, I agree with you. What I should say is that it makes onboarding trivial for the most common case, and they explicitly don't care about any less common cases (even if they are not all that uncommon).

Re: Encrypted email is still a pain

#439

Post by zeveb »

mikegerwitz wrote: post #392
zeveb wrote: post #229

Earlier quoted context omitted.

> 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 yo…

> 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".

Whom in the world do you actually trust to vouch for everyone else in the world? For me, at least, the answer is 'no-one,' — which is why neither XPKI nor the Web of Trust work for me.

> But it works for many others; it doesn't make it broken.

I suspect that no-one (older than, say, four years old) trusts any other human being or organisation to vouch for every other human being and organisation, and thus that the WoT is in fact broken for everyone — but that most folks just try to ignore that.

Re: Encrypted email is still a pain

#440

Post by jecxjo »

lol768 wrote: post #106
jecxjo wrote: post #65

The more this topic comes up, the more I start to wonder if the "difficulty" in email encryption is actually people just being lazy. We have IM and texting apps like Signal. You install, and if your friends install then you're secure. Most people skip verifying fingerprints, not doing IRL face to face verification. Yes the install process is simple and requires no real work to start encrypting things, but that still…

>I start to wonder if the "difficulty" in email encryption is actually people just being lazy I think it's a combination of this and perhaps some ignorance as to the implications of skipping these processes, hence they aren't taken seriously. I'm not sure if more education on this is the solution or not, since it seems a lot of people don't really care about these internals and don't want to take the time to understa…

I've had the "security" conversation with my father-in-law a few times. He is a wanna be computer nerd.

I tried to explain to him the benefits of all traffic being encrypted. It means "the man" can't see anything you are doing. Why would you want this? Because it sets a precedent that you aren't hiding something. I had a job once where coworkers only spoke Spanish when they wanted to talk about someone without their knowledge. It was obvious and even those who didn't speak the language could see it was happening. If they just spoke it all the time no one would have suspected they were making fun of someone, and no one would have paid that close of attention to what they were saying. It would have become a non-issue.

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