Everybody claims that GPG is unusable, but I just don't think that is the case. Thunderbird+Enigmail works perfectly hassle-free. You just enter your passphrase and everything else just works. The hard part about using GPG is convincing your peers that it's worth the minimal effort to set up. "I've got nothing to hide" is the common response.

Yes, for the technologically literate echo chamber of HN and most of our immediate peers, GPG may seem trivial to install. But the real people that have something important that needs to be encrypted (journalists, entire countries full of suppressed people, business secrets, etc) will NOT think this is trivial and most people will simply take their chances.

That doesn't mean that GPG is bad or that it isn't a strong tool, it means that for mass adoption then we need to make the tools easier to use.

My 60 dad, who has never managed to work well with computers (and has 4+ toolbars in IE, and likes them) managed to install GPG and Engimail in his Thunderbird, and managed to actually get them to work.

Without help.

If he can do it, anyone can.

Your last statement is just not true. My mother struggles to log into Facebook. "It works on the other computer". Yes, because the password is cached on the browser there; it's not on my laptop. "I'm putting the right password in but it's not working". No, you're not. Etc.

So are you arguing that facebook shouldn't have launched, because users exist who don't understand how to log in to it?

No, I'd certainly not compare a web service which nearly everyone uses - and for many is the only reason they have an internet connected device in the first place - with an encryption technology practically no-one uses.

Someone here suggested that "PGP isn't too hard - you just need to spend 30 minutes studying cryptography before you use it" which pretty much makes my case for me!

I'm sad that we've gotten to the point where asking users to make a small investment of time makes a product basically a non-starter. There's such a thing as too much convenience.

It really is hard to estimate ability within the general population by one example.

In any case, it would be much simpler to direct someone to Proton mail, which uses OpenPGP.

Proton mail doesn't support IMAP, 3rd party clients, or email export. If you decide you no longer want to use Proton but you want to keep some of your emails, you have to manually save the contents of each message. It's irresponsible to recommend Proton without mention of the commitment involved.

Oh yeah - lol - email clients. I remember them. No, the solution has to work seamlessly with gmail, yahoo, hotmail, outlook, whatever clients people are using. It needs to be everywhere or it might as well require a different protocol/client altogether.

Sure, if you only ever check your email from that one workstation, it's easy. That's not really how email works today. Most people expect their email to work seamlessly across multiple devices and OS's. Email would be useless to me if I couldn't use it on my phone.

My home workstation and my phone both talk to the same IMAP server (my home server). The phone has K-9 Mail and OpenKeychain on it; no trouble sending and receiving PGP mail at both locations. Not that I have anyone to send PGP mail to, since no one uses it...

Yeah, I've been there too. At the company I worked for a few years ago I tried to get everyone using PGP. One or two actually did. The problem is that while it's usually possible to set it up on a mobile device, it's not trivial, and you lose some important features. For example I very often need to search for an old email on my phone. If that email came in encrypted, then I'm not going to be able to find it if it's not stored on the phone. (Right? Was I just doing something wrong?)

The problem is the security of you GPG jey. If my phone gets hacked or stolen I lose my key. Sure, my master key is not on my phone (or my workstation) but still a big deal.

I use Yubikey Smartcard both on my workstation and on my phone. The setup works, but its both exepnsive, takes a long time to set up and its fairly difficult to do. Now that I have the setup, I can only use it with a few friends.

Keybase is working on a more scalable solution. Every device has different keys and messages are encrypted for each device. This allows them to revoke individual devices. While deploying this to most non technical people, is still quite a challenge, at least its an attempt at solving the multi device problem. I can at least imagen how with their approch we could get wide use, while with traditional gpg I cant really see it.

What does the average user do when they forget their passphrase? (Which they will do constantly.)

How do you determine the keys associated with the people you wish to communicate with? (The web of trust and going to key-signing parties are about a thousand miles from 'everything just works'.)

To be honest, I don't even see the point of setting a separate passphrase for your PGP on a machine you own if it adds any hassle for you [1]. I don't see why you PGP key should be so different from every other password you use. Sure, PGP does not have forward secrecy, but neither does gmail if someone grabs your password.

I agree with you that if you want to actually improve the security of the people who are right now not using any encryption, make encryption easy to use. Even if this means that it might not fit the threat-model of those targeted by state-actors.

IMHO, PGP could actually be used for this (even if it might not be the perfect fit) by using Trust On First Use, better interfaces and more integration into mail clients. The problem is that it is right now a tool used and made by those who want really strong security. This includes e.g. encouraging you to set a passphrase, which makes it more secure, but also more of a hassle for most people.

[1] This is obviously only true if you don't fear it being compromised / your security requirements are low. But then, if you need strong security, use full disk encryption and Qubes or something similar.

What happens if you lose control of your private key? How do you ensure the recipient keeps up to date with which keys have been revoked? Isn't it a risk that unless you keep changing keys you're at risk of someone getting your private key and having access to every message you've ever received?

I think installing a mail application is certainly well above the hassle threshold of most email users. Yes, it has to be that simple. If users have to generate or store a keypair, or install a mail client, then it won't happen.

So what do you think is the reason nobody uses PGP? It can't just be "nothing to hide" because people aren't struggling to disable encryption on the services which currently offer it. WhatsApp, imessage, HTTPS etc.

I don't use it because I don't put into a computer anything I wouldn't mind seeing on the front page of the Times. I lost the game before I even started playing.

same thoughts. I have been using GPG since the late 90ies and can't see the issues everyone has. But funny how that the same people who have no issues discussing some of the most complex things in CompSci e.g. functional programming, ML, AI, who write code in emacs and then say they hate pgp because it is too complex. Come on guys :-)

Maybe those people you list are smart enough to know PGP could and should be simpler.

Just because you can deal with complexity doesn't mean you should accept it, or seek it for that matter.

We're talking about your mum, not Emacs users. No one's suggesting the average HN reader can't manage PGP.

And then your mobile email UX is a disaster.

Then they should work on something better - the same way they worked on this new STS standard.

I think Adam Langley has already started such a project, but it's only been a "spare-time" project:

https://github.com/agl/pond

> because it's a user interface disaster

I'd rather explain this with necessity to learn concepts of public key cryptography, which takes time and efforts to understand. Most of people don't know about that and are not interested to know that. Interface is secondary issue: it won't take a lot of time to setup your keys given you know crypto.

My girlfriend have successfully passed the EFF's guide to PGP in half an hour (with a bit of my guidance), coping well with some inconsistences of the guide. https://ssd.eff.org/en/module/how-use-pgp-windows

There's "people who are happy reading about maths for half an hour before installing and configuring PGP" and "people who want to download an app as simple as Facebook messenger" and there's very little intersection between them.

For most people you're right. But that seems like just the type of challenge a billion dollar company could tackle. :)