Your dad is probably exactly the kind of person Zimmerman was thinking about in 1991. Somebody with one PC that they do everything on. He also has a specific mo

Your dad is probably exactly the kind of person Zimmerman was thinking about in 1991. Somebody with one PC that they do everything on. He also has a specific motivation for learning about and putting up with public key crypto. I don't know what UIs you've used, but the ones I've used dating back to the early 90s are nothing like what you're describing. Typical public key crypto UIs are very clear and unambiguous, and I've had no trouble teaching intelligent people how to use them. The problem is twofold: First, half the population is necessarily below average. Second, even getting the intelligent people to keep using it is a completely different matter. I've had an engineer-CEO mandate PGP usage for the company. Later, when sending him encrypted documents, he couldn't read them. Why? Because he'd gotten a new laptop. Where were his keys? Who knows. Ditto one of the best and most security-minded engineers I know. Tried to send an encrypted file to him, "I haven't really used PGP in years, I'm not sure where my keys are". I've kept a keychain[0] intact for the better part of a decade. I don't personally know a single other person who has, including the person who originally asked me to generate a public key. [0] In fact, one of my still-used SSH keys is also about that old, as is my known_hosts file. These are, again, singular accomplishments in my professional and social circles.