What will it take to get people using PGP for email?

You already identified the "usability" issues. It would need to be a system that required people to just get once a "code" for their computer. And then another systems auto detect if the recipients has also a "coded" machine.

Encryption is just inconvenient for the average user and doesn't provide some immediate benefit ("My bank needs encryption but I don't need to encrypt my funny cat pictures").

Addresimg the issue of key availability could be perhaps achieved by OS compatibility. Eg. If two Mac users send each other an email to iCloud addresses it can be encrypted by default and have iCloud manage the key exchange. This is just a thought on using the cloud as a part the key management similar to what Exchange does. It does not mean that is not hackable since compromising iCloud would compromise both clients but it could be a good start. Encryption by default among same cloud users.

You could adopt a company policy that mandates PGP for everyone as it's not that difficult to create, distribute and revoke public keys for your employees. Problems arise when you try to apply this process to the larger public, as that means having people self-sign their certificates for their public keys or having one user vouch for another. But that's where security breaks. Even with CAs on the internet you're never 100% sure you're talking to a legit entity; any scenario where CA aren't even present is just a nightmare that doesn't improve security by one bit. It's not just about making sure nobody except the recipient can read emails it's also about making sure that the recipient is legit, and that's the problem.

About usability. Well, I'm not an expert but runbox.com (with their roundcube interface) or unseen.is let you use gpg keys in a really easy way. They generate (or you can import) a pair of keys in the browser so they never have access to them. The only catch is that if you erase your cache or their cookies, you lost your keys and have to import them again. By default, runbox sends your public key as an attachment.

I think the sad truth is that not only is encryption inconvenient for most emails from most users. It is just not even necessary. So, you are trying to decrease convenience for...?

It is worse in the web world. I want someone to be able to index my emails. As I do actually search on them rather often.

Unless there is a homomorphic technology I'm not aware of (very possible) to allow searching over encrypted emails, then I don't know how you can get around the fact that there is a third party that has access to the unencrypted. Once that happens, game is over. Right?

I think it's a great question.

When I think about why I don't use pgp personally, and why I don't encourage others to use it (besides the fact that no else uses it) it's a functionality issue. I need to be able to access my email via my computer, phone, AND web browser (potentially not on a computer I own/control). My understanding is that is not easy to accomplish - maybe I've been misinformed. Until then, it's hard to start using pgp.

To answer your question, a good place to start might be a company like Good Technology - given their involvement in email solutions for so many large corporate customers.

Make email work exactly as it does now, but it is encrypted -- then people will use it. If you make it more inconvenient then it is a non-starter as email privacy from Google or the NSA just isn't a concern for 99.9% of people (stat made up).

PGP cannot encrypt the “subject” header or metadata like the “timestamp”, “to” and “from” fields.

https://www.gnu.org/philosophy/no-word-attachments.html

As an interim solution you can setup a secure contact form on your company website like https://encrypt.herokuapp.com/ - it encrypts the message before sending it to you.

Absolutely streamlined interface where they have to do pretty much nothing for it to work.

Here are some problems, from the top of my head, in no particular order:

  - Subjects can't be encrypted.
  - Encrypted mailing lists are complicated. Do you reencrypt in the middle?
    What software do you use? The mailing list manager you use right now probably doesn't support it.
  - Enigmail still doesn't support storing e-mails decrypted*. As a consequence, full-text search doesn't work.
  - There's also S/MIME.
  - Theres no software to manage public/private keys enterprise-wide.
  - Legitimate server-side email retention requirements for enterprises
  - Many people are quite alright with "most other people won't be able my email; maybe governments can".
  - Most emails quite simply aren't that important.
  - How do you deal with lost keys?
  - Webmailers
  - Often, as a sender at a company, you can not afford to inconvenience contacts.
  - No easy way to synchronize keyrings.
  - Server side spam filtering not possible
  - Out-of-office auto-forwarding
  - The other side uses gmail.
  - Your mother keeps asking why you aren't on Whatsapp.
  - The "metadata" (who mail whom? when? how long are the emails?) is quite telling.

Please solve all of these.

Sorry for the unreadable list. Thank pg for the shitty markup format.

First, somehow make popular email software developers (Thunderbird, Mail.app, etc.) to include OpenPGP support out-of-the box and make it easy to use. I.e. not a scary-looking interface hidden beneath 4+ clicks deep in settings, but a simple-to-get "security" button and an unobtrusive suggestion to generate or import a keypair on account creation. This is an absolute necessity. For webmail providers ask them to at least provide signature verifications for PGP-signed mail - that should be acceptable even for Gmail-like ad-based mail-sniffing business model.

Then, just start using OpenPGP. For every recepient with a known key encrypt the message, for others - sign it. Users will notice your emails have some fancy security-related icons and curiosity will eventually prevail.

Almost works with S/MIME for me (but since obtaining a certificate is not trivial - only "almost", not really).

You can make a seamless experience so that people don't even realize that their email is encrypted, but then the problem becomes: if their computer crashes and they lose their private key, they have now lost access to every previous email ever written. That's just unacceptable. I closely guard several backups of my private key, but most people aren't going to create an enormous single point of failure like that.

We have had a similar discussion in the past: https://news.ycombinator.com/item?id=6663098

It seems to me that S/MIME has a better chance for wide adoption due to it being built in to many email clients (Mail on OS X/iOS at least.) However it's still up to the user to get a certificate, which is a barrier. But I'm curious what others think, as I haven't seen S/MIME brought up in the recent encrypted email threads.

My highly cynical take: education. It will fucking take education.

All this "oh my god but PGP is so complicated, how can a regular user be expected to use all this?" thing is crap we use to delude ourselves into ignoring the fact that most e-mail users are too ignorant to understand why invasions of their privacy are so dangerous, let alone that it can be done or how.

Seriously, it's not complicated. There are a ton of everyday tasks that are far more complicated than setting up and using Enigmail, and yet average users do them every day. If people can set up a fucking network printer with HP's crapware, they can most certainly use a PGP plug-in for their e-mail client of choice.

PGP does have a lot of problems, from unencrypted subjects to usability problems with mailing lists and stuff. But it's still better than nothing, and if poor usability were such an important factor, Altair 8800 would have been the first and last PC.

But even if all these problems were to be solved, we'd still face the fact that the vast majority of e-mail users don't even know what a mail client is, don't understand just how widely-available the contents of their messages are, and don't really understand the far-reaching implications of them being available pretty much in the open.

And even after that, we'd have to face the even sadder reality that this is but a really tiny win in terms of privacy, because convincing people to use PGP is nothing compared to convincing people to stop using Facebook, Google and webmasters to stop using the tracking shit that fills 90% of the post-web 2.0 pages.

> Gmail seems like an obvious entry point ... but it would go against their business model (they could no longer mine your emails).

A few ideas why google won't mind encryption that much:

http://www.reddit.com/r/tech/comments/278cze/google_launches...

> Is there any hope?

TextSecure is already offering a secure communication service(that in my view could be a decent replacement for email). They will also release a browser extension in the future. Those(and the fact google's involved) are good signs for google's encryption project , at least technically.

And assuming the technical infrastructure for easy encryption does exist, i can see some sort of hybrid model[1] becoming popular and/or mandated in some groups, and growing from there.

[1]For example, textSecure/redPhone's model lets you send sms to everybody, but if it detects the other side has encryption , it encrypts it. There's also an easy to use method for out-of-band key verification.

Suppose, hypothetically, that there was some kind of ultra-phishing virus that resulted in a 1/100 chance of losing money as a result of sending unencrypted email ... people still wouldn't use PGP. They'd switch to facebook messenging or SMS or something.

It's just too much hassle. People don't use it unless they absolutely need to. Signing is slightly more common, and might be easier to bootstrap.

Start by signing your mail. We might be able to persuade banks and other phishable businesses (e.g. Paypal) to start signing mail too. That gets the keys in place.

You mention gamification; some sort of automated system that hands out rewards or does something useful if you send it a PGP-signed mail might be a way to do this.

IMO, the issue is that real security is inconvenient, and my email is just not that secret.

The problem will all come down to UX.

* Key generation and exchange is a challenge. Most people I have taught how to use gpg / pgp can't seem to figure out how to publish there keys, send or receive keys.

* Entering your password often is a pain. Most people I have taught have given up using this on a day-to-day basis because its just such a pain.

As an aside, there's the problem of improper use. Right now there are too many choice as to how you can setup pgp leading to the problem of people using it wrong. And don't get me started on private key security. Most people do NOT want to think about this. Quite honestly, I agree. Something needs to be done to make it very hard to compromise your own private key.

Here's a scheme I've been thinking about. It's an opportunistic PGP setup:

1) Whenever you want to send an email you look up the PGP certificate for the domain (yes domain) you are sending it to in some central keyserver. If you find it pin that certificate for future use and sign and encrypt the email. If you don't find it just send a normal email, possibly still signing it.

2) For a sysadmin to start using the scheme just publish a public PGP key in the central keyserver and when you receive an email that's encrypted with your domain key decrypt it and deliver it to your user.

This buys you a few things. For large hosting providers (say Gmail) you get a little better security than the current SSL between mailservers setup because it's harder to MitM and can be relayed between mailservers without security issues. You also get a PGP signature attesting that the email does indeed come from @gmail.com and isn't spoofed. Individual users that care can then use this scheme to get user-level encryption by having email in their own domain @myname.net. You could even outsource the @myname.net mail server to a normal POP/IMAP provider and publish the PGP key to the central server yourself. The provider then gets the encrypted mail and you decrypt it locally in your mail software.

But maybe relaying doesn't really happen these days and fixing STARTTLS would give you most of this with SSL certificates instead.

I agree with the points people here have brought up. For my part, I think it would be good to at least have a seamless OpenPGP interface with at least signing enabled for all mails (if encryption not always possible), and I'm working on https://autonomail.com to that end. Other folks (like https://whiteout.io) are also working on similar solutions.

In a large company, such a change only has a chance if it is mandated from the top and then the mgmt team is very committed to push the change through for as long as it takes. Without both pieces it will get killed by apathy at the middle management layer and below. Without that support the technical solutions will gain no foothold.

When people/media/govt/everyone is/are still arguing whether the surveillance state is merited or not, whether Snowden is a traitor or not, a technical solution is meaningless. The argument over whether it needs a solution needs to be "solved" or at least agreed on enough that their is an "issue" to be "solved" anyway.