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I'm giving up on PGP

blog.filippo.io

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Re: I'm giving up on PGP

#31

Post by LongTermBond007 »

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 thing that could ever be imagined. I have seen a video called “Gigantic Martian Insect Party,” and I have seen another video called “Gigantic Martian Insect Party 2: Don’t Tell Mom,” and I hated both videos, but this did not stop me from directing the sequel “Gigantic Mar- tian Insect Party Into Darkness.

This is hilarious, thanks for pointing this out!

Re: I'm giving up on PGP

#32

Post by dom0 »

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 Trust implies such a glaringly obvious visual metaphor that I am truly in awe that not a single program works that way.

Tabulations of keys are not a WoT, period.

I don't verify keys one-by-one, that's bullshit. I get one good key that's part of a WoT, and then go from there, and can easily see from the web structure that other keys are good and what their relations are. None of that is accomplished by any PGP frontend.

Instead I get stupid and unhelpful error messages ("no key available" - I just downloaded it!) and some of the most terrible crypto UI I've seen ("How much do you trust this key? [ ] Not at all [ ] A bit [ ] Fully [ ] Totally" - w-t-f).

A technical criticism of PGP/GPG is of course also possible. The whole thing is a museum of early 1990s crypto, with default ciphers like CAST5 and messages not being authenticated - and even if the message is authenticated most parts of the PGP protocol are not, meaning that you got that big bunch of C code maintained by that one German guy over there that parses unauthenticated bytes that you shipped through half the internet with a big neon-red sticker on it saying "I'M PGP PLEASE TAMPER WITH ME".

Re: I'm giving up on PGP

#33

Post by Freak_NL »

kkl wrote: post #8
mixedCase wrote: post #2

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/

The author of the article mentions Signal as well, but how do you handle communication from a laptop or desktop computer and/or with people who don't own an Android or IOS smartphone?

Re: I'm giving up on PGP

#34

Post by JulianMorrison »

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'm going with fundamentally flawed. Or perhaps more exactly, a solution for a non-problem.

Things PGP can do:

- Hide the contents of a message. But not the fact of a message nor who it's to. And it's only as hidden as a key that your recipient has to keep secret indefinitely.

- Permanently be incriminating, since the message can be as easily opened a decade from now.

- Prove you're you. Which is great for incriminating you. Also the proof is only good if your secret key is still secret, which probably isn't the case if you've been arrested. At that point, it's good for convincing people it's you when it's really the FBI.

- Authenticate keys through a trust mechanism so sparsely populated that unless you're actually in a spy cell, the chances of having a valid trust path from A to B is astronomically small.

- Distribute keys through what is really only slightly more sophisticated than a world-writable Dropbox.

Re: I'm giving up on PGP

#35

Post by esseti »

I've been using PGP for mostly 1 year and yes, I agree. I still send around signed email, but never received one encrypted so far. Generating keys and backing them up is tricky and I have probably made mistake in generating or storing them at some point in time. Is there a step-by-step good-practice on how to use PGP?

Re: I'm giving up on PGP

#37

Post by psiconaut »

rakoo wrote: post #24
psiconaut wrote: post #4

Earlier quoted context omitted.

A few projects that I'm aware of (disclaimer: I'm involved with LEAP): - https://pixelated-project.org/ - https://www.mailpile.is/ - https://modernpgp.org/memoryhole/ - https://inbome.readthedocs.io/en/latest/ - https://leap.se/ Edit: btw, if you're in Berlin from 14-18 Dec, drop by the AME2016 unconf+hackaton https://github.com/mailencrypt/ame2016

That's a very nice list of links and overlaps with some idea I had, thanks a lot ! INBOME in particular looks to me to be (part of) the way forward, is there any way to follow progress ?

some discussiong going on in the ame2016 ML: https://lists.mayfirst.org/mailman/listinfo/ame2016

you can also track the repo: https://github.com/mailencrypt/inbome/

Re: I'm giving up on PGP

#38

Post by coherentpony »

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…

Is keybase open source?

Re: I'm giving up on PGP

#40

Post by parennoob »

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-...

I agree, a lot of services displayed a shocking amount of incompetence in that post. However,

a) The more proofs you have, the harder it becomes to force them. YC for example is one location, and is run (in my opinion) by very smart people where it would be hard to get a compromise.

b) My point is that this is an excellent alternative to not using anything in a way that is both friendly to people ("just make this post on [website]") and compatible with an older, better method of privacy (PGP) that people have been using for years.

It may not be as perfect as some of the more esoteric alternatives that people have suggested elsewhere in the thread (I'm not sure about this, can an incompetent phone company employee compromise some of the phone-based ones? I've come across a lot of incompetent phone company people), but much easier for the regular person to use.

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