[nailer]

> "Making email and PGP easier to use is not only a UX issue."

Yes, but UX is still the biggest issue. By all means develop next gen crypto tech: but first, make what we have now usable by people who aren't Unix people.

I would pay money for binaries of an Open Source GnuPG for OS X which wasn't awful to use.

Not in a tarball, not assuming I want to use the command line, on gnupg.org (with the angry SHA1 certificate warning fixed), not linked to from there for 'people who want GUIs'.

[hedgehog]

The problem runs deeper than UX in plugins for mail clients. Offline key exchange is inconvenient enough that it prevents GPG from being used as encrypted-by-default mail. Identity and key management is really the underlying issue, something in the spirit of CONIKS might be good enough to build a working system though. As OP points out even then you have issues with multi-device support.

[digi_owl]

While offline exchange is needed for proper security, for casual snoopers having a the clients generate the pair, embed the public in every outgoing, grab publics from incoming, and encrypt by default for outgoing from that point on, would be a major step up from the status quo.

[Programmatic]

> Offline key exchange is inconvenient enough that it prevents GPG from being used as encrypted-by-default mail.

I would love to simply sync users' keys between their devices and encrypt opportunistically like OTR does. Offline key exchange would only be necessary for verification purposes at that point. I see user key management as the harder problem than exchange.

[nailer]

> The problem runs deeper than UX in plugins for mail clients.

UX runs deeper than software interfaces.

> Identity and key management is really the underlying issue

Yes, that's a UX issue.

So:

- Get GPG key from Facebook (which has them as part of the standard profile today)

- Say to person: you should contact this person by a means you trust and confirm this is their key (since we don't trust anyone by default).

- Once they click OK, they can now send messages to that person.

Nothing stopping other mainstream sites from adding GPG, it's jus that FB is the only one I know of. Obviously GitHub doesn't count since most people aren't software developers.

[zbyte64]

Which brings us back to trusting a 3rd party to not tamper with the key exchange...

[nailer]

Well yeah, that's why I addressed it in the post you're replying to. Offline key confirmation is still the best bet for most people, it's just that people don't use it because they don't use crypto because crypto tools are awful.

[aroch]

That's what GPGTools is for (formally MacGPG): https://gpgtools.org/opensource.html

(You can build and use your own gpg binaries if you're concerned about their modifications)

[nailer]

GPGTools is precisely the awful state of current of affairs I'm talking about.

- GPGTools isn't sure what's called. GPGTools? OK where do I download GPGTools? There's no button to do that. What's GPGSuite? Do I want that instead? Installed, there's nothing called either Applications/GPGTools or Applications/GPG Suite.

- Its app is called 'GPG keychain' or similar. Nobody outside crypto folk care know what a keychain or, not should knowledge of a keychain app be required to send someone a message encrypted with their public key

- The apps main focus is key management, and it's really poor at that. There's no way to discover people's GPG keys AFAICT

- It's a plugin for Apple Mail and a command line app. Most people using Macs don't use either of those. And it's not promoted as a Mac mail plugin, which means most people will be disappointed when they use it.

- It seems to choke on common GPG output with some chars. That output is probably not encoded correctly, that shouldn't matter. Be liberal in what you accept.

[aroch]

1) If installing something is enough of a hurdle that you can't complete it, then no amount of simplification beyond bundling is going to solve that

2) Everyone and their mother understand that keychains hold keys. You have to get to a key somehow, the onboarding process is a simple wizard. Again, if you can't follow prompts to enter an email, enter a password, and wiggle your mouse around; no amount of simplification is going to solve the problem.

3) You use the search for key button...

4) I'd argue that the vast majority of Mac users, especially the ones that are not technically inclined enough to use GPG on cli but want to, use the built in Mail.app.

5) gpg seems to have a slew of text encoding gotchas, I'm not sure how those can be fixed without a lot of core dev effort

[oceanofsolaris]

I think that your points 2) and 3) are not perfectly reasonable if you really want to reach those who are not yet using encryption.

If you look at how keychains are usually used nowadays, they are an implementation detail you could and probably should hide from non-technical users.

As you say yourself, in order to find a key, you use the search for key button. Which prompts the program to look on a keyserver. You then import the first non-expired key you find for the desired email address. Why not do this automatically? You just annoy users who have to go through two (highly non-self-evident) steps and who do neither know nor care what a 'key' is. They just want to write secure email to their friends. (and btw, does the key-search even go over a secure connection with a pinned certificate? Because else you are not even trying to avoid MITM attacks).

Is it too much to ask these users to read the manual, learn about which kind of key is the most secure yet also compatible with the GPG versions of their friends, find out how many bits theirs should have, have them wiggle their mouse (why, couldn't you use /dev/urandom for most cases?), upload their key to a keyserver, search their friends key from a keyserver, learn about the web of trust and go to a key-signing party? Is this too much to ask? Probably yes. I did not need to acquire a similar amount of knowledge about TextSecure and yet it probably transmits my messages in a more secure form than GPG.

I am not saying that key-discovery is super-easy and all these are completely solved problems. But why do you have to make it so much more complicated for users than it has to be?

[aroch]

PGP is not supposed to be TOFU, friction to adding/trusting keys is part of the point of PGP -- verification of trust.

If clicking a prominently placed button to lookup a key is not intuitive, then how do these users manage the just as unintuitive process of finding, verifying, and installing an application on their device?

Keys are searchable over HTTP/HTTPS, and the HTTP derived (insecure) hkp and TLS-secured hkps protocols. The whole point of PGP is that you don't trust the source of the key without verification, so the protocol over which you receive the key doesn't matter.

There exist a plethora of implementations that hide the trust-building exercise from users, and they're all for instant messaging. You can shoe horn that into email, but why? PGP is based on the web-of-trust principle of verification; if you just want the attestation that UserX probably owns KeyX, use a service that's tied to your phone number or email that doesn't use PGP -- i.e. textsure, telegram, whatsapp, etc.

[oceanofsolaris]

At least the GPG authors seem to be of the opinion that in order to make their programm usable for a larger amount of users, TOFU would be a good idea [1]. I don't see why hiding the trust-building from users is necessarily such a bad thing if it leads to a lot more people using encryption. If you are an expert user, verifying the keys is not impossible for you, even if GPG uses TOFU.

In the end, the current PGP workflow is simply unusable for many people [2]. It might be a good idea to introduce a new and improved encrypted email protocol, but since PGP/GPG are already here and had a lot of developement, why not make them usable for more people? What percentage of your emails are currently sent encrypted? I have currently two people whom I can send encrypted email; 99% of my email is currently not encrypted. I would really love to increase this.

[1] https://www.gnupg.org/blog/20150911-gnupg-this-summer.html

[2] Edward Snowden had a hard time convincing Glenn Greenwald to set up GPG. Even though he made a 12 minute video that detailed all the (horribly unintuitive for a non-expert) steps. So even with a strong incentive (possible whistleblower contact), the difficult setup procedure was enough to scare Greenwald away.

[nailer]

1. Installing software is easy. People do it all the time, it's actually a very mainstream thing now. There are app stores built into most things. People know what apps are, and don't have trouble finding or downloading them.

Installing GPGTools or gpgbanana, or whatever it wants to call itself at present however is hard.

2. Stand on street corner and offer free coffee to anyone who can explain what a keychain is.

3. Last time I checked there was no way to find an arbitrary person's pubkey in GPGTools. What directories does it use?

4. I'd say most use gmail. Mail server headers would back that up.

5. I can fix most with sed. If you see a bunch of equals signs and Unicode values, replace it with the equivalent Unicode character.

[aroch]

1) Clicking a button that says download is too hard? I'm confused by the mythical people who want encryption but are too dumb to follow a software installation paradigm that's been around for probably longer than they've been alive. Fine, search the appstore for an [proprietary] app: http://imgur.com/a/WbuZA . How exactly does this address your original issue of wanting OSS that's verifiable?

2) I could but I would go broke in minutes. 99/100 people would reach into their pockets or purses and pull out a ring full of keys and would intuitively understand that their computer uses an application to do similar. If your faith in people is so low you think they're all morons, why bother encrypting what they have to say. They're idiots anyways, not like they have enough mental capacity to plan anything according to you.

3) By default it uses either pgp.net or MIT's hkp servers, I can't recall. Most public keyservers sync their directories multiple times a day. You can search by name or email: http://imgur.com/a/SSHlP

4) How does using gmail prevent you from using the built in Mail.app or have anything to do with the headers not including gmail stuff? OSX provides a system-wide onboarding process for linking your gmail to all the system apps...

5) So you can send user generated input that doesn't match what they wanted to send. How is that helpful?

[nailer]

I started reading your comment, but you're attacking a straw man: nobody has ever said clicking a button was hard.

Additionally you think people who don't understand software that's complex to find or install are 'dumb'.

I stopped reading there. You should reconsider how you think about others.

Edit: you've edited your post and added some screenshots of the app store. Fine, I'll bite. There are good things in the App Store, this doesn't address the fact that the GPG site won't point you to any of them at all, that GPGTools has multiple names and the download link is off the front page, that MIT is not a mainstream directory of people, that knowing about keychains being a popular requirement for crypto does not means that it is necessary, or any of the other massive flaws in crypto UX as exists today that I haven't already addressed.

You said "Everyone and their mother understand that keychains hold keys." then agreed this wasn't true, and then twisted that so claim that I think people are morons. If you're not trolling (if you are, you're doing very well playing someone who has no sense of sympathy), you're missing the point: other people don't care about crypto, they just want privacy. Much in the same way you don't care about rack and pinion steering, you just want to go somewhere. That doesn't make them morons, it makes them busy.