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I'm giving up on PGP

blog.filippo.io

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Re: I'm giving up on PGP

#151

Post by lmm »

sqeaky wrote: post #123
lmm wrote: post #113

> Yeah, about that. I never ever ever successfully used the WoT to validate a public key. If you ever installed a Debian package then you did. A long-term identity as "Bob Jones" might not be terribly useful - but that's not the kind of long-term identity we care about a lot in real life either. A long-term identity as "Debian release manager" or "Signatory on bank account xyz" or even "Wikileaks committee member" is…

You understand the difference between a lone hacker as an APT vs a state level threat as an APT. That distinction is huge and chooing not to defend yourself against one or the other may allow for huge convenience gains at the cost what is to many a purely hypothetical notion of security. Can we improve the tools and techniques we have enough so they are convenient enough to not have to make such a choice?

What do you mean by "APT"?

Re: I'm giving up on PGP

#152

Post by ranko »

lmm wrote: post #151
sqeaky wrote: post #123

Earlier quoted context omitted.

You understand the difference between a lone hacker as an APT vs a state level threat as an APT. That distinction is huge and chooing not to defend yourself against one or the other may allow for huge convenience gains at the cost what is to many a purely hypothetical notion of security. Can we improve the tools and techniques we have enough so they are convenient enough to not have to make such a choice?

What do you mean by "APT"?

"Advanced persistent threat"; see also https://en.wikipedia.org/wiki/Advanced_persistent_threat

Re: I'm giving up on PGP

#153

Post by lmm »

floatrock wrote: post #141
lmm wrote: post #117

Earlier quoted context omitted.

Innovative new ways of distributing PGP key fingerprints are to be welcomed. But why would you not keep using PGP for the part that it's good at?

The author did include the standard UX-of-PGP-sucks arguments, but he was also making the point that some of the core models around PGP suck. eg he was saying you can't share a key across multiple devices. Or if you do, you just increase your attack vector and your weakest link becomes the hotel wifi you plug into. eg if your key does get compromised, now you have to rotate all your contacts, which if you distributed…

> eg he was saying you can't share a key across multiple devices. Or if you do, you just increase your attack vector and your weakest link becomes the hotel wifi you plug into.

So what are the options here? You can have a GPG key protected by any mechanism you care to think of (passphrase, smartcard, ...). You can share it between devices or not as you see fit, subject to the same tradeoff that is always going to be involved in that decision. I can't see any way to do it better?

> eg if your key does get compromised, now you have to rotate all your contacts, which if you distributed your key on a business card, is pretty friction-prone and encourages you to discount that weird activity that could have been a blip you saw on the hotel wifi.

PGP actually has very good support for key rotation by using subkeys - you keep your master identity key offline/secure and that's what other people sign, but you use it only to sign subkeys with short expiry times. People don't use it, but that's a UX issue.

> The big one is if your key ever does get compromised, now all your past history becomes accessible. So he's saying there's some things that PGP is fundamentally bad at, and you need a new model, not just a band-aid UX fix.

True, but I think long-term signing is often what you want. There are different models that make sense for different communication scenarios certainly.

Re: I'm giving up on PGP

#154

Post by halvdan »

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.

Haven't used it for communication but I've been using it as a means to store encrypted backups with a cloud provider.

If you're interested, check out duplicity at http://duplicity.nongnu.org/.

Re: I'm giving up on PGP

#155

Post by nickik »

stinkytaco wrote: post #145
nickik wrote: post #120

Earlier quoted context omitted.

Well, you can have your GPG Private Key online if you like, but thats not my point. The new system moves away from having any sort of master key. Rather every device has a new key, and they all sign each other. You can add new devices without old proves being invalidated. See: https://keybase.io/blog/keybase-new-key-model and https://saltpack.org/ I would really like a solution using this stuff that is highly integra…

That's an interesting solution. Rather than having keybase keep your key, your devices are communicating directly to validate each other? I'm going to have to review this in more detail, thanks.

Currently you have to use a paper key to do it. You then upload a public prove chain. Its not where it should be yet, but the concept is pretty good.

Re: I'm giving up on PGP

#156

Post by sickbeard »

module0000 wrote: post #92

PGP may have broken down for the author, but it's still used in a lot of places . For example, to communicate with our bankers at work, every email has to be properly encrypted and signed - or it goes into a blackhole. The only way to exchange public keys(initially) is in person. Once that is done, new keys are provided from that person, and the WoT expands. tldr; it doesn't work for the author, but it does work for…

In otherwords, it only works in controlled environments, not out in the wild

Re: I'm giving up on PGP

#157

Post by CalChris »

I think his security threat model was nation state when he really needed APT, annoyingly persistent teenager. There are elements of what he did that I'd do if they were automated. But if the NSA, Mossad, Hacking Team want to get me, they're going to get me. And it would only be vanity to say they are even thinking of me.

So this is the perfect being the enemy of the good. I need good privacy and good security. I'm not going to torture myself for perfect privacy and perfect security. Cut to the last scene of The Conversation where Gene Hackman's character tears apart his office ripping down the walls to find the bug and the eavesdropper taunts him. Who is torturing whom?

Re: I'm giving up on PGP

#158

Post by ihnorton »

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 in the first place?

I'm fairly naive to this area, but wouldn't video chat initiated with public keys suffice? Then confirm identities and exchange secrets. To me this seems substantially equivalent to in-person key exchange for non-Three Letter Agency threat models. 20 years ago this wouldn't really have been feasible, but today it (mostly) is -- from a quick glance at the FAQ, Signal may even support something like this already.

(If your threat model includes "abduction and coercion", then aren't you kind of hosed even with previous in-person OTPs?)

Re: I'm giving up on PGP

#159

Post by Nadya »

JulianMorrison wrote: post #110
Nadya wrote: post #102

Earlier quoted context omitted.

1) Key rotation can solve the second part of this. 2) Key rotation solves this, but you lose the ability to read old messages yourself. If you don't have the keys anymore you can't view the message. 3) This isn't unique to PGP? Or do you have an alternative? Because plaintext is infinitely less secure in this regard. 4) Depends how you determine trust of a user. In an ideal world you'd be correct. But I trust the per…

Missing the point a little bit on 4. Proving you're you is great if you're, say, Canonical distributing package updates to Ubuntu, where the adversary is malware distributors. But where your adversary is eg: the FBI, then it promotes a false sense of assurance, because it's actually really easy to spoof someone if you can arrest them and force them to give the key password.

>because it's actually really easy to spoof someone if you can arrest them and force them to give the key password.

Country dependent [0]. Not enough evidence one way or the other for FBI coercing.

[0] https://en.wikipedia.org/wiki/Key_disclosure_law

Re: I'm giving up on PGP

#160

Post by gkya »

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 it done.

And he complains he don't get encrypted mail. So what, I'd rather be happy. It'll be useful when it'll be w/ email, and has many other uses otherwise.

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