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I'm giving up on PGP

blog.filippo.io

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Re: I'm giving up on PGP

#71

Post by kkl »

NoGravitas wrote: post #45
kkl wrote: post #8

Earlier quoted context omitted.

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/

Signal is nice, and I use it. But it's an instant messaging system. Email has different use cases. I think what we're going to need is a new, non-SMTP protocol, which preserves all of the good things about email, while providing e2e encryption and (pseudonymous) identity assurance. I don't know enough to be involved in designing that protocol, though, other than saying what I want to see as an end-user.

What properties does email have that asynchronous messaging services (e.g. Signal) do not?

Re: I'm giving up on PGP

#72

Post by rbcgerard »

erelde wrote: post #28
rbcgerard wrote: post #19

Usability is the "key" - it's hard enough to get people to use signal ("why do I need another messaging app?")

If they don't have Signal you could get them to either use Whatsapp, or only use the encrypted conversation feature of Facebook's Messenger. They should have one or the other already installed if they're complaining about "another messaging app".

Very true, i do default to WhatsApp quite often, but not being in FB's eco system is something I'd like to avoid (especially given the the privacy bargain that comes with both)

Re: I'm giving up on PGP

#73

Post by m3ta »

FiloSottile wrote: post #55
m3ta wrote: post #48

There isn't a lot to unpack in this article. Most is set-up; explaining how connected he is to a community that is enthusiastic about PGP yet doesn't apply secure operations in practice. Then there is the main complaint: > I haven't done a formal study, but I'm almost positive that everyone that used PGP to contact me has or would have done (if asked) one of the following: > - pulled the best-looking key from a keyse…

That is definitely not my main complaint, and I suspect it might have caught your eye because it's the one that wouldn't apply to you (which is absolutely possible). The article is about the flaws of long-term identity keys, and it would stand even if there weren't UX, adoption, or security protocols adherence issues. Maybe try to unpack a bit more :)

You're right, long-term identity keys are bad. Long-term identity keys are not a concept mandated by PGP, they are a result of how people use PGP or how PGP is implemented in a third party app.

No part of PGP requires you to use a key more than once. This phenomenon is a result of a consensus of people deciding on a terrible operations strategy over a long period of time.

Edit: this comes to mind https://gist.github.com/grugq/03167bed45e774551155

Re: I'm giving up on PGP

#74

Post by UweSchmidt »

jerf wrote: post #13
psiconaut wrote: post #3

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…

"How do you distribute the one time pad "

Well you hand it over to the person you want to communicate with when you see them?

Obviously that doesn't work in many use cases, but in many other cases it does: many of the most important secrets are typically shared with people you already know and have met before, no?

Re: I'm giving up on PGP

#75

Post by xxdesmus »

jgrahamc wrote: post #15
keeganjw wrote: 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.

I typically send 3-5 per week.

Re: I'm giving up on PGP

#76

Post by nickik »

stonemetal wrote: post #22
parennoob wrote: post #9

To me, Keybase ( https://keybase.io ) seems to solve the "PGP has a bad user experience" problem correctly for like 90% of the population. You post proofs of your public key to known media (Twitter, Github, your website, etc.) which you control. These can be checked by anyone. Even if the remote person doesn't know they are talking to you (as a human entity), they know they are talking to the combined online persona…

The combined online persona of those accounts is only as strong as their combined security. aka: Why would services need to collude when they can get the job done by ineptitude? https://medium.com/@N/how-i-lost-my-50-000-twitter-username-...

This is a crazy story but I still think Keybase gives you a lot to defend here. You have to compromise all the accounts and change all the proves to actually be able to send valid messages to somebody else.

That is a tall order, even if you use the same email as a username everywhere. I use long random passwords and 2Fa on a number of the important accounts. I don't trust google and Facebook, but I trust them to have some interest in not letting accounts be compromised.

Also if somebody changes all the proves, they will all be new and a smart system should be able to detect this sort of stuff in the future.

Re: I'm giving up on PGP

#77

Post by Arathorn »

The conclusions here (avoiding long-lived per-identity keys and having the option to easily rotate and re-validate per-device keys) are very much what we've aimed for in the end-to-end crypto for Matrix.org (https://matrix.org/blog/2016/11/21/matrixs-olm-end-to-end-en...).

Rather than using a silo like Signal or WhatsApp, it is possible to get the flexibility of an open federated network built on an open standard, whilst still having the lighter weight approach of trust common to E2E messaging apps like WhatsApp. Or at least that's the hope :)

Re: I'm giving up on PGP

#78

Post by dublinben »

smhost wrote: post #64
dom0 wrote: post #32

Earlier quoted context omitted.

> I wonder if pgp is fundamentally flawed, or we have a deep conceptual usability issue here. I don't think the "WoT" is conceptually flawed, and frankly, the argument that "people of average intelligence" can't grasp the concept comes from a very high horse and is also untrue. It's simply that any and all software for PGP utterly fails in the UX and functionality department when it comes to key management. Web of Tr…

The standard for adoptability isn't the average person at their peak hours of attention and focus. It's the drunk teenager at 2 in the morning fumbling around in the dark.

A functional WoT should be no more difficult to use than managing your Facebook friends or contacts on your phone. Neither of those are difficult tasks, and are achieved by normal users every day.

Re: I'm giving up on PGP

#79

Post by CoryG89 »

mixedCase wrote: post #61
CoryG89 wrote: post #11

Earlier quoted context omitted.

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…

Lavabit didn't do E2E or at least stored the user's keys; since the owner did in fact have the keys needed to unencrypt the Snowden e-mails (and sent them to the FBI in paper using infinitely small character size, apparently).

IIRC, they did not store user's keys. What they wanted was for Lavabit to turn over their SSL key, which would have compromised security for the entire service, rather than just targeting Snowden specifically.

Presumably they did not have the ability to turn over the emails themselves, so they wanted Lavabit to provide a vector to do a man in the middle attack.

Re: I'm giving up on PGP

#80

Post by sdenton4 »

UweSchmidt wrote: post #74
jerf wrote: post #13

Earlier quoted context omitted.

"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…

"How do you distribute the one time pad " Well you hand it over to the person you want to communicate with when you see them? Obviously that doesn't work in many use cases, but in many other cases it does: many of the most important secrets are typically shared with people you already know and have met before, no?

Like when I buy a new laptop from new egg, or contact Laura Poitras with a hot scoop...
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