As part of my book’s chapter on end-to-end encryption I’ve been writing about the horrors of PGP.

As a recap of what’s bad with PGP:

• No authenticated encryption. This is my biggest issue with PGP personally.
• Receiving a signed message means nothing about who sent it to you (see picture below).
• Usability issues with GnuPG (the main implementation).
• Discoverability of public keys issue.
• Bad integration with emails.
• No forward secrecy.

For more, see my post on a history of end-to-end encryption and the death of PGP.

(excerpt from the book Real World Cryptography)

The latter two I don’t care that much. Integration with email is doomed from my point of view. And there’s just not way to have forward secrecy if we want a near-stateless system.

Email is insecure. Even with PGP, it’s default-plaintext, which means that even if you do everything right, some totally reasonable person you mail, doing totally reasonable things, will invariably CC the quoted plaintext of your encrypted message to someone else (we don’t know a PGP email user who hasn’t seen this happen). PGP email is forward-insecure. Email metadata, including the subject (which is literally message content), are always plaintext. (Thomas Ptatcek)

OK so what can I advise to my readers? What are the alternatives out there?

For file signing, Frank Denis wrote minisign which looks great.

For file encryption, I wrote eureka which does the job. There’s also magic wormhole which is often mentioned, and does some really interesting cryptography, but does not seem to address a real use-case (in my opinion) for the following reason: it’s synchronous. We already have a multitude of asynchronous ways to transfer files nowadays (dropbox, google drive, email, messaging, etc.) so the problem is not there. Actually there’s really no problem… we just all need to agree on one way of encrypting a file and eureka does just that in a hundred lines of code.

(There is a use-case for synchronous file transfer though, and that’s when we’re near by. Apple’s airdrop is for that.)

For one-time authenticated messaging (some people call that signcryption) which is pretty much the whole use-case of PGP, there seems to be only one contender so far: saltpack. The format looks pretty great and seems to address all the issues that PGP had (except for forward secrecy, but again I don’t consider this a deal breaker). It seems to only have two serious implementations: keybase and keys.pub. Keybase a bit more involved, and keys.pub is dead simple and super well put. Note that age and rage (which are excellent engineering work) seem to try to address this use case. Unfortunately they do not provide signing as Adam Caudill pointed out. Let’s keep a close eye on these tools though as they might evolve in the right direction. To obtain public keys, the web of trust (signing other people keys) hasn’t been proven to really scale, instead we are now in a different key distribution model where people broadcast their public keys on various social networks in order to instill their identity to a specific public key. I don’t think there’s a name for it… but I like to call it broadcast of trust.

For encrypted communications, Signal has clearly succeeded as a proprietary solution, but everyone can benefit from it by using other messaging apps like WhatsApp and Wire or even federated protocols like Matrix. Matrix’ main implementation seems to be Riot which I’ve been using and really digging so far. It also looks like the French government agrees with me. Same thing here, the web of trust doesn’t seem to work, and instead what seems to be working is relying on centralized key distribution servers and TOFU but verify (trust the first public key you see, but check the fingerprint out-of-band later).