Filippo Valsorda is an engineer on the Cloudflare Cryptography team, where he's deploying and helping design TLS 1.3, the next revision of the protocol implementing HTTPS. He also created a Heartbleed testing site in 2014. This post originally appeared on his blog and is re-printed with his permission.
After years of wrestling with GnuPG with varying levels of enthusiasm, I came to the conclusion that it's just not worth it, and I'm giving up—at least on the concept of long-term PGP keys. This editorial is not about the
gpg tool itself, or about tools at all. Many others have already written about that. It's about the long-term PGP key model—be it secured by Web of Trust, fingerprints or Trust on First Use—and how it failed me.
Trust me when I say that I tried. I went through all the setups. I used Enigmail. I had offline master keys on a dedicated Raspberry Pi with short-lived subkeys. I wrote custom tools to make handwritten paper backups of offline keys (which I'll publish sooner or later). I had YubiKeys. Multiple. I spent days designing my public PGP policy.