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Ask HN: Why is PGP not used widely?

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Re: Ask HN: Why is PGP not used widely?

#51

In my experience it is mostly due to annoyance. PGP is seamless until someone tries to check their mail on their friend's computer and discovers that encryption works as intended . Then all of a sudden they start begging you not to send them encrypted messages. I have yet to see any other reason for why PGP is not even used by people for whom it would be easy. Even within the security and cryptography research commun…

I know some folks in the Air Force - all of their ID cards have public/private keys stored on them. They use them (plus a pin) for logging onto their computers at work, all of their e-mails are digitally signed, and the computer is locked just by removing the card from the card reader. Most personnel don't know a thing about public key encryption/two factor authentication, and likely wouldn't care if you offered to e…

Wikipedia gives better overall picture in TL;DR fashion. http://en.wikipedia.org/wiki/Common_Access_Card

Re: Ask HN: Why is PGP not used widely?

#52
For two reasons: because it has a UX that hasn't changed meaningfully since the mid-1990s (GUI tools for GPG/PGP tend simply to wrap the command line UX), and because it presumes that the only reasonable way to use a tool like GPG is to exert fine-grained control over keys and identity.

Email needs to be encrypted opportunistically, without user intervention. GPG could do this; it could generate semi-ephemeral keys as needed and use key continuity, like OTR, to figure out which keys were kosher for which addresses.

Instead, GPG exposes to its users the metaphor of a "key ring" with different kinds of keys and key signatures. That model works for people like me, who use it to secure corp-to-corp communications where I have very specific and fussy requirements for whose keys I'm interacting with. But it doesn't work for end-users at all.

Someone should write a secure-by-default email client that uses the OpenPGP message format and is compatible with GPG, but that ignores the intended GPG security model entirely.

Re: Ask HN: Why is PGP not used widely?

#53
Without meaning to detract from some of the excellent explanations in this thread, I should add that it sounds like you're approaching this as if it were mostly a technical problem when as far as I can tell it is mostly a social problem. Social problems are harder than coming up with a tool to make it understandable, although I strongly suspect that's also not as easy as you think it is. The failure modes, corner cases, and generally making it robust to someone who Just Doesn't Get it are what kill you, not the happy path of a user who does roughly what they ought.

Setting aside the social problems of explaining cryptography and generating a network effect, most people assume their communications are not worth listening to. "If they want to listen to/read my mom drone on, they're welcome to it!" Or they assume it happens to "someone else."

I'd expect that most people -- rationally and correctly, I might add -- conclude that it's unlikely to happen to them in any way relevant to their experience.

Anything you suggest has to overcome that inertia. Facebook was a value-add. Cryptography's value-add is subjectively nil and possibly negative (whoops laptop stolen lost my keys) if you don't see the benefit in the first place.

Re: Ask HN: Why is PGP not used widely?

#54
1) Most people haven't had a need for it. Till now. 2) Encryption is difficult concept for even technical people. 3) Commercial PGP costs too much. Building a quality PKI system for an organization costs more 4) GPG is a pain to use 5) Encryption has been discouraged by the government, companies and users.

Re: Ask HN: Why is PGP not used widely?

#55
post #52

For two reasons: because it has a UX that hasn't changed meaningfully since the mid-1990s (GUI tools for GPG/PGP tend simply to wrap the command line UX), and because it presumes that the only reasonable way to use a tool like GPG is to exert fine-grained control over keys and identity. Email needs to be encrypted opportunistically, without user intervention. GPG could do this; it could generate semi-ephemeral keys a…

Yup. I have made an active use of GPG over the last few months, and there's a few big problems:

1. A UX that is... Hard. As you say. See the last few minutes of this talk I did: http://youtu.be/LjZk8PP-u3c

2. You can't PGP with webmail.

3. You can't PGP on mobile.

4. This means that unless you're on your desktop, you can't do things like search through older emails, which is really important.

5. It requires both people to use PGP.

I fully agree with your final sentiment. If I could fork myself, this is one of the things I'd be putting a ton of time into.

Re: Ask HN: Why is PGP not used widely?

#56
post #48

Earlier quoted context omitted.

The problem with the key exchange mechanism you've described is it's untrustworthy. The software would be essentially asking "is this initial email from the person you think it is?" which is a tough question to answer given the fact that emails can be readily spoofed. Granted, Bob's key will differ from Mallory's key, but there may be just enough time to do bad things before detection. Key exchange between people sho…

> Key exchange between people should always require some kind of offline verification. If you don't do this, you can't really trust that the person you're communicating with is who they say they are. I know a lot of people who I've never met IRL and likely never will. When you think about it, I already don't know that they are who they say they are. Many of them live far from me. I don't see a practical way to exchan…

This is why theres the web of trust concept. Which is even harder to explain than public/private keys.

Re: Ask HN: Why is PGP not used widely?

#58

I think it's because there still isn't a good metaphor that covers up the complexity of public key encryption. Such a metaphor is a prerequisite for a UI that the average user can comprehend. First, I think we should rename the keys to 'locking key' and 'unlocking key'. I've had people still scratch their heads at 'public/private' a few days after I've completely explained the concept to them. They find it easier to…

The problem with the key exchange mechanism you've described is it's untrustworthy. The software would be essentially asking "is this initial email from the person you think it is?" which is a tough question to answer given the fact that emails can be readily spoofed. Granted, Bob's key will differ from Mallory's key, but there may be just enough time to do bad things before detection. Key exchange between people sho…

> Key exchange between people should always require some kind of offline verification.

Or a trusted third party (see IBE.)

Re: Ask HN: Why is PGP not used widely?

#59
It's fairly easy to get a good working PGP system on OSX - Symantec makes it obscure to get but it works well, at least for file encryption with options available in the Finder menu.

https://www4.symantec.com/Vrt/offer?a_id=109355

No need to pay - you just need to go through the rigmarole of getting a trial registration.

Re: Ask HN: Why is PGP not used widely?

#60
post #59

It's fairly easy to get a good working PGP system on OSX - Symantec makes it obscure to get but it works well, at least for file encryption with options available in the Finder menu. https://www4.symantec.com/Vrt/offer?a_id=109355 No need to pay - you just need to go through the rigmarole of getting a trial registration.

I'd highly advise against this and instead suggest going with GPGMail or similar. Considering the NSA's documented influence on security companies, an encryption product from a large corporation is quite possibly the worst choice you could make.
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