An alternate title for this post would be "Why GPG isn't ok in 2017".
Imagine you were designing a new encrypted messaging system, what kinds of things would you worry about? You'd want to make sure you were using good encryption algorithms, authentication for senders, a high quality random number generator, maybe you'd spend some time thinking about side channels for things like message length. Unfortunately, if you're thinking about your protocol in the context of something like email, it's very likely that you're not thinking about forward secrecy.
GPG is a textbook example of this. GPG's cryptographic model is centered around long-term RSA keys. I get your public key from a keyserver, I generate a random AES key and encrypt that key with your public key, and then I encrypt my email with the AES key. When you receive my email, you decrypt the AES key with your RSA private key, and then you decrypt the contents with the AES key. So what's the problem? RSA is a solid algorithm, AES is a solid algorithm, if we use modern key size and padding it's strong against any attacker, no one can decrypt these messages or crack the key.
The problem is that if anything happens to our private key, even years later, it can ruin the confidentiality of our messages. Imagine I send you a GPG encrypted email. Someone's recording all of my TCP traffic, but it's not a big deal because the message is encrypted. Then a year later, your hard drive gets stolen, and with it your GPG key. Now our attacker can use that to go back in time a year and decrypt the email in the recorded traffic from a year ago. People tend to rotate their GPG keys incredible infrequently (arguably, this behavior is incentivized by the web of trust model, which demands a persistent key), so these keys live for a decade or more, putting all the data encrypted with them at risk.
Luckily, modern message protocols solve this problem. The most famous (and widely deployed) of these protocols is the Signal Protocol, which is used by Signal and WhatsApp. The Signal protocol uses the Diffie Hellman key exchange to achieve Forward Secrecy. This means that every message is encrypted with a fresh key, and then that key is thrown away. An ephemeral key exchange is used to get the key to your peer, but all of its parameters can also be thrown away as soon as it's finished. Morever, the Signal protocol does one of these on every single message you send. This means if I steal the key used to encrypt one of your messages, I can't decrypt anything that came before it (I can decrypt things that come after it though). There's also no long term key you can steal and decrypt everything with. Because of this, forward secrecy is often defined as using long term keys for authentication, and short term keys for encryption.
However, I think this undersells the importance of forward secrecy. Because forward secrecy means being able to delete your message. Right now, if I delete an email that's been GPG encrypted to me, I haven't really deleted anything. The attacker who steals my email still has it (there's always an attacker, that's why I encrypt things). The only way to make sure that email is gone for good is for me to delete my GPG private key permanently. With a forward secure messaging system, I can delete any messages I want and as long as my chatting partner deletes them as well, they're gone for good, no keys lying around for years, putting my privacy at risk.
It's popular to make fun of the security guarantees of SnapChat, since they're in no way resistant to a malicious chatting partner. But the ability to securely, and meaningfully, delete messages is a huge win for many threat models. Whether you're a dissident whose phone is being searched by a repressive regime, or a White House employee whose phone is being searched by your boss, you want to be able to delete your messages.
The TLS ecosystem has been making this exact migration to protect user privacy. Current versions of TLS offer two forms of key exchange, RSA key exchanges with this major drawback, and Diffie Hellman key exchanges which offer forward secrecy. The upcoming TLS 1.3 specification completely drops the RSA key exchange, making TLS always forward secure.
And this is why I say GPG encryption isn't ok in 2017, there's no ability to delete messages without deleting my key, and deleting things is critical to protecting my privacy. This criticism doesn't just apply to GPG of course, almost all "secure email systems" are built on the same cryptographic choices, which offer no forward secrecy. If you're designing a new secure messaging system, use forward secure protocols to protect your users' privacy. If you're choosing a messaging system to use, stick to ones with a forward secure protocol (such as Signal) to protect your privacy.
PS: You can donate to support Signal's development.
Hi, I'm Alex. I'm currently at a startup called Alloy. Before that I was a engineer working on Firefox security and before that at the U.S. Digital Service. I'm an avid open source contributor and live in Washington, DC.