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I'm giving up on PGP

blog.filippo.io

11–20 of 350 posts

Re: I'm giving up on PGP

#11

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

There is a reason they mostly don't exist, at least in the US. After Lavabit was so publicly shut down, it's going to be a losing proposition for anyone to put so much time and effort into it, just to then be given a choice between providing a backdoor or shutting down as soon as the government realizes they can't break your service.

If your going to start such a service, it needs to be in a country that will respect free speech. And there aren't many.

Re: I'm giving up on PGP

#12

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

Why not S/MIME? Most clients support it, its stupid easy, and has had a lot of eyes on it considering its age.

Constantly re-inventing email encryption seems to be the problem here. None of them really make this stuff any better. Key distribution is still going to be PITA, but sticking with a supported standard makes the most sense.

Re: I'm giving up on PGP

#13

I find very interesting the point about the split between what WoT was supposed to be, in theory, and what little it represents, in practice, in terms of practices about key verification. It has been said many times that the lack of adoption of pgp in mail was due to the average user not being able to grasp the concepts behind the proper operation for key management, but the article points to common practices among "…

"I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here."

I think it's the key model that's fundamentally flawed rather than pgp itself, which I believe the author of the article is also asserting.

In cryptography, it is often explained that despite the fact a one-time pad is guaranteed-secure (given various conditions I'm eliding), it is not practical in the vast majority of cases because of a chicken-and-egg problem: How do you distribute the one time pad in the first place? If you do it insecurely, it's a waste of time. If you can do it "securely", why not just use that secure channel to send the message in the first place? OTPs can still be useful because you can establish a secure channel once for a limited duration of time and then use it to temporally shift your security into the future, but that's a relatively rare use case. (That is, the vast bulk of encryption is being used between people who may never have had a "secure" channel between them; think HTTPS here.)

Similarly, PGP's got this significant problem where given that you have the correct keys and that you know you can trust them, it secures your communication quite effectively. But the question is, how do we get to the point where you know that you have the correct keys and you can trust them? Well... that's a hard problem itself. Especially considered over time.

So alternate models must be pursued.

Like the author, I think the Keybase approach is a good idea. In fact I'd even suggest that the idea should be generalized away from "social media accounts" to just "potentially unreliable mechanism" in general. If I have 6 mechanisms for asserting identity on my key, each of which are 95% reliable over the course of a year, then from an absolutist security point of view, that key is still insecure... but assuming even modest independence between the unreliable mechanisms (assuming naive total independence is definitely incorrect, once one is hacked the others are certainly more likely, but neither is it the case that one hack guarantees all others can be hacked), it's still much more secure than nothing at all.

Re: I'm giving up on PGP

#14
I've been thinking a lot about PGP and other encrypted messengers lately. It's incredibly hard to get a lot of people to agree on one messaging app besides default SMS. I wish there was an open source suite of tools for mobile/desktop that easily layered PGP on top of SMS/email experience and would fall back in the absence of keys. Perhaps bluetooth for swapping keys with friends. It's something that needs to be seamless enough that the end user can't tell the difference. I don't think messaging encryption will achieve mass adoption until something like that is built or built into mobile OS's.

Re: I'm giving up on PGP

#15
post #5

After all that, he was only getting two encrypted emails a year! Damn. That's crazy.

This has been my experience. The only "good" experience I've had with encrypted messages through email was a back and forth exchange I had with a fellow Keybase user where I manually copy and pasted blocks of encrypted text into/out of their web interface.

Re: I'm giving up on PGP

#16

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

Google's End-To-End also seems dead.

https://github.com/google/end-to-end

I would say ProtonMail or the miniLock-based Peerio.com are now the most interesting projects for encrypted email.

EDIT: https://minilock.io/

https://github.com/PeerioTechnologies/peerio-client

Re: I'm giving up on PGP

#17
post #8

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

Most interesting e2e projects have abandoned email, specifically SMTP, as a secure messaging platform. I would look outside SMTP-based solutions if I were to start using a different project (assuming doing so is an option... I hope it is!). My recommendation here is Signal: https://whispersystems.org/

A big problem is that a lot of this is driven less by people who have a genuine need for encrypted communication and more by people who want one on principle. And the latter tend to include the people who are more likely to try The Next New Thing.

And it also makes sense. A lot of these services are from companies that need to make money. And there isn't much money in the journalists and dissidents who don't have a bespoke solution.

Re: I'm giving up on PGP

#18

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

Doesn't cover "default", but mailvelope is a project working on making email for real people (i.e. webmail) easy to secure. I use it often. https://www.mailvelope.com/

Requires private keys to loaded into the browser extension. No thanks! Google's E2E is the same, which is to, say garbage.

Re: I'm giving up on PGP

#20
post #16

Dark Mail seems to be dead. Are there any efforts to make e-mail secure by default and e2e encrypted?.

Google's End-To-End also seems dead. https://github.com/google/end-to-end I would say ProtonMail or the miniLock-based Peerio.com are now the most interesting projects for encrypted email. EDIT: https://minilock.io/ https://github.com/PeerioTechnologies/peerio-client

Private keys accessible to the browser is the worst model. I don't think this was ever taken seriously at Google either...
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