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I'm giving up on PGP

blog.filippo.io

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Re: I'm giving up on PGP

#51

Post by acqq »

LongTermBond007 wrote: post #31
eriknstr wrote: post #21

Good points, but also I would like to point out that https://www.usenix.org/system/files/1401_08-12_mickens.pdf linked from the blog post was an entertaining read so for anyone that didn't read said PDF, do.

> “But James,” you protest, “there are many best practices for choosing passwords!” Yes, I am aware of the “use a vivid image” technique, and if I lived in a sensory deprivation tank and I had never used the Internet, I could easily remember a password phrase like “Gigantic Martian Insect Party.” Unfortunately, I have used the Internet, and this means that I have seen, heard, and occasionally paid money for every thi…

I like:

"It’s like, websites are amazing BUT DON’T CLICK ON THAT LINK, and your phone can run all of these amazing apps BUT MANY OF YOUR APPS ARE EVIL, and if you order a Russian bride on Craigslist YOU MAY GET A CONFUSED FILIPINO MAN WHO DOES NOT LIKE BEING SHIPPED IN A BOX. It’s not clear what else there is to do with computers besides click on things, run applications, and fill spiritual voids using destitute mail-ordered foreigners. If the security people are correct, then the only provably safe activity is to stare at a horseshoe whose integrity has been verified by a quorum of Rivest, Shamir, and Adleman."

For his claim "YOU’RE STILL GONNA BE MOSSAD’ED UPON" I still don't know how to interpret the fact that Snowden seems to be relatively fine. Maybe that he had the idea about the blind spots of the system in which he worked.

His opinion on PGP "web of trust":

"“Chains of Attestation” is a great name for a heavy metal band, but it is less practical in the real, non- Ozzy-Ozbourne-based world, since I don’t just need a chain of attestation between me and some unknown, filthy stranger— I also need a chain of attestation for each link in that chain. This recursive attestation eventually leads to fractals and H.P. Lovecraft-style madness."

It is an opsec problem that all the connections are then cryptographically provable.

Re: I'm giving up on PGP

#52

Post by ReverseCold »

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".

This works fine until you get someone who only uses iMessage, and you use Android.

Re: I'm giving up on PGP

#54

Post by pricechild »

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…

Have you tested your group of people?

Re: I'm giving up on PGP

#55

Post by FiloSottile »

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 :)

Re: I'm giving up on PGP

#56

Post by ReverseCold »

WorldMaker wrote: post #41
keeganjw wrote: post #5

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

The deepest I ever got into active PGP/GPG was in college (where it is certainly easiest to have WoT key signing parties) and so far as I recall none of us ever really bothered encrypting anything to each other, we just signed a most of our emails as something of a prideful badge that didn't really mean much all things told. (To the point where at least one friend made a joke fake PGP signature that wouldn't verify t…

Relevant: https://xkcd.com/1181/

Re: I'm giving up on PGP

#57

Post by psiconaut »

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.

pond has interesting properties, I think the next generation mail will have to implement some of those ideas.

and Signal/WhatsApp comes to replace (and kill) xmpp, not email. Another issue is the generational shift away from email, that is only for Spam and Work, more and more everytime...

Re: I'm giving up on PGP

#58

Post by heartbreak »

milge wrote: post #43
erelde wrote: post #26

Earlier quoted context omitted.

Carriers would need to change the way they handle SMS, and everything a carrier does is subject to state regulations. And states seem to like clear text.

Why's that? I understand the message would increase in size because of the encryption, but I think it would be technically feasible now. Didn't even apple just introduce encryption into their messenger? My issue with apple's encryption is it's closed source and apple only.

iMessage end-to-end encryption is not a recent introduction. It has been in place for several years, though I can't find the exact iOS version it was introduced in.

Re: I'm giving up on PGP

#59

Post by cabalamat »

dom0 wrote: post #32
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 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…

> 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.

I disagree. I have written email encryption software, and I find WoT complicated.

In light of this recent article on HN https://news.ycombinator.com/item?id=13111768 I suggest you re-evaluate the level of ability of the average user.

Re: I'm giving up on PGP

#60

Post by milge »

heartbreak wrote: post #58
milge wrote: post #43

Earlier quoted context omitted.

Why's that? I understand the message would increase in size because of the encryption, but I think it would be technically feasible now. Didn't even apple just introduce encryption into their messenger? My issue with apple's encryption is it's closed source and apple only.

iMessage end-to-end encryption is not a recent introduction. It has been in place for several years, though I can't find the exact iOS version it was introduced in.

Recent to me is the last few years, technology-wise. Your timeline may look different.
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