Secure E-Mail is an Impossibility

A while back I wrote a handful of introductory guides on using Pretty Good Privacy (PGP) to encrypt the content of your e-mails. They were well intentioned guides. After all, everybody uses e-mail so we might as well try to secure it as much as possible, right? What I didn’t stop to consider was the fact that PGP is a dead end technology for securing e-mails not because the initial learning curve is steep but because the very implementation itself is flawed.

I recently came across a blog post by Filippo Valsorda that sums up the biggest issue with PGP:

But the real issues I realized are more subtle. I never felt confident in the security of my long term keys. The more time passed, the more I would feel uneasy about any specific key. Yubikeys would get exposed to hotel rooms. Offline keys would sit in a far away drawer or safe. Vulnerabilities would be announced. USB devices would get plugged in.

A long term key is as secure as the minimum common denominator of your security practices over its lifetime. It’s the weak link.

Worse, long term keys patterns like collecting signatures and printing fingerprints on business cards discourage practices that would otherwise be obvious hygiene: rotating keys often, having different keys for different devices, compartmentalization. It actually encourages expanding the attack surface by making backups of the key.

PGP, in fact the entire web of trust model, assumes that your private key will be more or less permanent. This assumption leads to a lot of implementation issues. What happens if you lose your private key? If you have an effective backup system you may laugh at this concern but lost private keys are the most common issue I’ve seen PGP users run into. When you lose your key you have to generate a new one and distribute it to everybody you communicate with. In addition to that, you also have to resign people’s existing keys. But worst of all, without your private key you can’t even revoke the corresponding published public key.

Another issue is that you cannot control the security practices of other PGP users. What happens when somebody who signed your key has their private key compromised? Their signature, which is used by others to decide whether or not to trust you, becomes meaningless because their private key is no longer confidential. Do you trust the security practices of your friends enough to make your own security practices reliant on them? I sure don’t.

PGP was a jury rigged solution to provide some security for e-mail. Because of that it has many limitations. For starters, while PGP can be used to encrypt the contents of a message it cannot encrypt the e-mail headers or the subject line. That means anybody snooping on the e-mail knows who the parties communicating are, what the subject is, and any other information stored in the headers. As we’ve learned from Edward Snowden’s leaks, metadata is very valuable. E-mail was never designed to be a secure means of communicating and can never be made secure. The only viable solution for secure communications is to find an alternative to e-mail.

With that said, PGP itself isn’t a bad technology. It’s still useful for signing binary packages, encrypting files for transferring between parties, and other similar tasks. But for e-mail it’s at best a bandage to a bigger problem and at worst a false sense of security.