I'm giving up on PGP • Hacker News Board

Re: I'm giving up on PGP

#201

Post by loup-vaillant » Tue, Dec 06, 2016, 8:33 PM UTC

pdkl95 wrote: post #140

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 in the first place? Something I've wanted to make for a while now, that should be possible to make with almost any cheap embedded microcontroller, is a hardware dongle that stores OTP pads. This would be a generic character device that could be integrated into existing chat programs. * Each device has a hardware RNG, e.g. [1] or similar * A port that allows two devices to conn…

You don't need to store a true one time pad. Keystreams are enough. So, while your device may act like it delivers a one time pad, it could instead draw a pseudo-random sequence from a chacha20 stream. That way, any synchronisation you do lasts for life.

But if we go to all this trouble, we might as well use public key cryptography, it's even easier to use. Internally, the dongle will be quite complicated, with stuff like Curve-stuff, Xchacha-something and poly-whatnot. What the users needs to know is simple:

Once initialised, your Dongle can publish a public a "fingerprint" that is unique to it. To decrypt messages encrypted with this "fingerprint", you need your dongle. To sign messages according to this "fingerprint", you need your dongle. If you lose it, your "fingerprint" becomes unusable, no recourse. If it gets stolen, the thief will be able to impersonate you, unless you did the sensible thing and locked your dongle with a secure passphrase (think Diceware).

Now we engineers can figure out how to make that dongle easy to use and secure against any compromised computer it may be plugged in. (We don't want the dongle to become untrustworthy just because it got out of your sight during lunch).

Re: I'm giving up on PGP

#202

Post by gliese1337 » Tue, Dec 06, 2016, 8:37 PM UTC

tscs37 wrote: post #172

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…

>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…

> It might be worthwhile to bring Signal (or at least the idea) to other protocols like E-Mail.

I'm glad to see someone else thinking the same way as me on this! I got myself an idea for Yet Another Secure Messaging App a while back. After a little market research, I kinda decided, well, everything that I want to do can already be done by PGP, or Signal, or Whisper... except that where they are easy to use, they don't integrate with e-mail, and where the integrate with e-mail, they are not easy to use. So, there's still room for more diversity in the market of providing easy-to-use secure, verifiable messaging, especially without trying to replace e-mail wholesale like so many messaging platforms (secure and otherwise) do. And maybe I'll actually get around to building it someday.

Re: I'm giving up on PGP

#203

Post by gkya » Tue, Dec 06, 2016, 8:49 PM UTC

camiller wrote: post #177

gkya wrote: post #160

What's this? But seriously what is this? I use GnuPG and am quite fond of it. I've a pubkey.asc up my website, and I use gpg to encrypt some files and my backup tarballs. PGP is not a mail tool, it's for encrypting strings. Yhis guy does not know what it is and cries for having done much ado for nothing. Key signing parties? I certainly have better things to do. Just generate a key and put it on mit key server, call…

He clearly knows what it is. He isn't ranting against PGP he is ranting against the WoT. If you got an encrypted email from Linus Torvalds, how would you verify it was him? https://news.ycombinator.com/item?id=12296974

I wouldn't. If I'm going to get an encrypted mail from someone, I've alread verified the sender.

Re: I'm giving up on PGP

#204

Post by dom0 » Tue, Dec 06, 2016, 8:50 PM UTC

acqq wrote: post #51

LongTermBond007 wrote: post #31

Earlier quoted context omitted.

> “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…

> 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.

What reason would any agency have to un-live Snowden? Any damage he has done was already done in HK and before; he has nothing more to reveal. It would only turn public opinion against the agencies.

Re: I'm giving up on PGP

#205

Post by vacri » Tue, Dec 06, 2016, 8:58 PM UTC

devilsavocado wrote: post #107

People who use PGP keys, can you give examples of your use? I'm genuinely curious. Who are you contacting, or who is contacting you? The author says he only receives 2 encrypted emails a year. Not only do I not have a PGP key, I don't think I've ever found myself in a situation where it was even an option to use one.

Signing .deb packages. Debian and its derivatives are core users of gpg as it's basically a requirement to sign installation packages - if the user doesn't have the key in their trust store, they get a big fat warning when they try to install said package.

Re: I'm giving up on PGP

#206

Post by XorNot » Tue, Dec 06, 2016, 9:00 PM UTC

lbenes wrote: post #193

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…

I worked in IT for an engineering company that required all external emails to be PGP encrypted. Despite all engineers having Symantec PGP software installed and setup, training, and support of IT, they would often ignore this policy. The excuse, often valid, was it would require IT from both companies to setup the encrypted keys for the first time for new users. If the system is too complex for engineers, the idea o…

99% of crypto would work just fine if you appended an OTR-like protocol over the top of email.

First email is "hey we're interested in blah..." and is sent in the clear. Then have the message window change color as subsequent emails get the protocol more secured.

Re: I'm giving up on PGP

#207

Post by XorNot » Tue, Dec 06, 2016, 9:01 PM UTC

bisby wrote: post #87

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…

Yeah. It takes some reading to understand the different levels of trust for a key. Even rewording those levels could be effective, if perhaps a bit verbose. []Distrust []Trust only this key []Trust this key to automatically trust other keys []This is my key Obviously I dont know what all the levels exactly mean. but as far as I can tell, these are the levels of "web of trust", where for it to truly be a web, #3 shoul…

There's also context. I trust the government to represent my bank. I don't necessarily trust it to represent my friends etc.

Re: I'm giving up on PGP

#208

Post by tscs37 » Tue, Dec 06, 2016, 9:03 PM UTC

gliese1337 wrote: post #202

tscs37 wrote: post #172

Earlier quoted context omitted.

>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…

> It might be worthwhile to bring Signal (or at least the idea) to other protocols like E-Mail. I'm glad to see someone else thinking the same way as me on this! I got myself an idea for Yet Another Secure Messaging App a while back. After a little market research, I kinda decided, well, everything that I want to do can already be done by PGP, or Signal, or Whisper... except that where they are easy to use, they don'…

The easy part is the crypto, that's been done to death and back.

Signal has managed to do the "How can we exchange keys while atleast one of us is always offline?" part. So a good and somewhat PFS key exchange should be possible too.

Integrating that seamlessly with email is gonna be hard and require a service to register emails or domains that support the new protocol. Otherwise you end up with the PGP situation.

One want people's mail to automagically encrypt when both have it. Automagically is the best security there is for Joe Average. On the big list of security problems you face for Jane Average, "Werks Automagically" is Point 1 written in golden ink by the pope himself in 72pt fontsize and "Secure against State Adversaries" is Point 2 written in silver by the pope's cat on the second page in 16pt fontsize.

One might also want to introduce a benefit, like disabling it for spammers by having some kind of verification (Phone Number or something?) and heavily police HTML formatting so that little Green Icon next the email means more than "this one spent 30 seconds to find a large prime pair" and more like "this email is probably safe to open, nobody will track you and nobody is going to sell you fake viagra".

People should want to use it, not have to use it to be secure or something.

But as you said, that all requires work and 99% of my time I personally like being unproductive, so I guess it'll never happen.

Re: I'm giving up on PGP

#209

Post by user5994461 » Tue, Dec 06, 2016, 9:03 PM UTC

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 have to partially disagree with that.

Calling PGP an utter failure is an understatement. Just like calling a cat a small tiger.

PGP is possibly the WORST experience in usability for any well known software that ever lived.

This thing should be taught in courses for decades to come as how to fail a product by 1) having no UI 2) no integrations with anything 3) zero usability 4) not even trying to give a fuck about normal users 5) in fact, not even trying to make it possible to use for advanced users.

---

You want signed email & identities. It's simple.

Just get the national government to distribute RSA USB keys to every citizen. Then they can use them on public government websites (taxes & jobs stuff) to confirm poeple's identities, just plug in the key. Quick and simple. (And that's not incompatible with ALSO asking for a password that was send in a different paper letter. 2FA-style.).

Then later, citizens can sign the emails they send to everyone with gmail/hotmail because they'll add the feature to recognize the national USB identity key, now that there are X millions people using it.

Re: I'm giving up on PGP

#210

Post by nshepperd » Tue, Dec 06, 2016, 9:07 PM UTC

JulianMorrison wrote: post #34

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 incriminat…

> - 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.

So, best practice: publish your private signing key publically if you ever get arrested?