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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#281

Post by drdaeman »

mjevans wrote: post #274
drdaeman wrote: post #67

Earlier quoted context omitted.

> the key retention is the biggest issue. You need to keep your key around for a long time, probably storing copies of it. As I get it, this one is a fundamental issue, not specific to messaging at all, but is just a secure storage problem. You either keep a copy of the message (and need some key to decrypt it, unless you keep it unencrypted), or you throw it away. No amount of engineering can solve this.

That's what 'perfect forward security' is intended to solve. For more details please look up the Off The Record (otr) protocol overlay. The basic idea is that any given session is authenticated temporally; when a session is completed the details for it are leaked so that anyone could forge content as having been within that session. Thus there is reasonable doubt about anything that was said/transferred having actual…

No. PFS is about when messages are in transit. Sure thing, it makes sense to encrypt them with ephemeral keys rather than a long-living ones.

However, that particular point I've quoted was - as I understood it - about message archives. Short-lived keys are just fundamentally incompatible with long-term storage. We either keep data, or we don't.

PFS helps for about another point raised, "if a key is broken or leaked..." (but has a trade-off, as it requires some sort of key exchange)

Re: Encrypted email is still a pain

#282

Post by Nelson69 »

tptacek wrote: post #75
problems wrote: post #62

Earlier quoted context omitted.

> No, I fully understand the problem. If Google Mail vanished tomorrow, a pretty large number of people would probably stop emailing altogether. The number of people for whom that's true increases every year. I highly doubt that's true. Email is pretty essential to the functionality of the internet, from signing up accounts to getting notifications, to just plain discussions with professionals. It's pretty much the o…

Three responses: * Email remains important for middle-class Americans because it's used for business. But that is a small subset of the whole population, including very large numbers of Americans. * For almost all those users, email might as well be a Google, Yahoo, or Microsoft product. * Every year, the number of people and businesses that rely on email gets smaller --- in the last 5 years or so, by something like…

Can you qualify that third point?

What's considered reliance? What's the name of some place that stopped using email? I can see a drop in businesses that are running their own email, and that outsourcing maybe represents a big shift in terms of how they see it as "not critical and must be kept in house" but I don't know that they rely upon it much less.

How are these businesses messaging and communicating?

Re: Encrypted email is still a pain

#283

Post by rmoriz »

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…

I've tried to collect some S/MIME resources (corporate users, software support etc.) in some GitHub gists available at http://smime.io/ - however the recent "ousting" of StartSSL hurt the (free) S/MIME adoption for individuals and neither LE nor Google CA are an alternative yet.

Re: Encrypted email is still a pain

#284

Post by Cyph0n »

yosamino wrote: post #131
Cyph0n wrote: post #97

Earlier quoted context omitted.

And if you were aware that a state-level actor is targeting you, you'd be using a programmable, self-contained HSM for all sensitive computation. This is a topic I'm working on actually.

That sounds interesting. Do you have anything you could share on the topic ?

It's still in the early stages honestly. I will probably share more after the first paper is published.

Re: Encrypted email is still a pain

#285

Post by WalterBright »

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 its way into most peoples' email, whether they are aware of it or not.

I know the metadata will still be plaintext, but if I am sending my tax return to my accountant, I don't really care if someone discovers that I am sending my tax return, but I do care that the tax return is encrypted. And I would demand that my accountant upgrade his email client.

Re: Encrypted email is still a pain

#286

Post by xorcist »

tptacek wrote: post #93
mikecb wrote: post #87

Earlier quoted context omitted.

If you are an active target of a tier 1 state, your endpoint will be compromised, your decrypted communication will be read, and no cryptosystem will prevent this.

Furthermore, if you're using PGP to evade a state-level adversary, the odds are overwhelming that you've own-goaled yourself many times over: * You keep plaintext archives and drafts of your messages, because that's a fundamental feature of email clients going back 3 decades. * You use a server-mediated PGP provider like Protonmail that has your security one surreptitious Javascript injection on an XHR call away from…

> You keep plaintext archives and drafts of your messages, because that's a fundamental feature of email clients going back 3 decades.

Name one PGP-enabled MUA that actually does this? None of the popular ones (mutt, enigmail, claws) do it. They didn't do it in the 90s, because that would have been stupid, and they don't do it now.

You could have said indexing and search if you wanted to point out actual usability problems with PGP-enabled MUAs.

Re: Encrypted email is still a pain

#287

Post by dang »

boomboxy wrote: post #144

Isis? I guess we have to trust her after all the ioerror affair, right? Considering he's currently on trial for all her allegations. /sarcasm moxie HAS to agree with his protocol. thegrugq? Wasn't he selling exploits to the highest bidder? http://www.forbes.com/sites/andygreenberg/2012/03/21/meet-th... I can't argue about their qualifications, I argue about their morality. .edit added link.

Please don't. This crosses more than one line and can't lead anywhere good.

We detached this subthread from https://news.ycombinator.com/item?id=13635827 and marked it off-topic.

Re: Encrypted email is still a pain

#288

Post by Jach »

nickpsecurity wrote: post #112

Let me contrast the author's experience with my own. Note that I had a brain injury during this process that made me forget scripting and GPG plus hard to learn. I'm a nice test case for how hard things are. :) So, I looked into GPG. Holy shit there's a ton of options and complexity. High-assurance security says subset to minimal thing that works for increased trustworthiness. I noticed it could encrypt files with ot…

I made this pretty quickly: http://kuuv.io/i/L4rZomr.png Slower than if I just used Python with tkinter since I wanted to learn a new UI framework with Clojure at the same time... But it's literally just a dropdown and some buttons wrapping some system calls to 'gpg'. I never bothered with the 'decrypt file' since I can remember 'gpg --decrypt' easily enough. :)

So I agree using GPG isn't very hard, it's easy to make it even easier for yourself, and I think its usability flaws are overblown. Unfortunately as a comment further up said "the GPG CLI acts exactly as I expect it to...and I don't expect non-advanced users to use it." Only advanced users use the CLI these days. Not because it's particularly complex or hard or a poor experience, they're just given no reason to, and no training even if they had reason.

Re: Encrypted email is still a pain

#289

Post by cdelsolar »

lmm wrote: post #172
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? 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…

Hm?

if /BEGIN PGP SIGNED MESSAGE/.test(message) { greatFirewall.block(message); }

Re: Encrypted email is still a pain

#290

Post by Arathorn »

anigbrowl wrote: post #277
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.

Riot might be a great platform for doing business, but it's pretty useless for any other kind of activity. If you're a political activist having an app called 'Riot' on your phone or computer is not going to look good to anyone in law enforcement.

well, it's FOSS; someone could maintain a fork with a less controversial name (I hear 'vector' is up for grabs O:-)
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