I've been using Enigmail for about a decade, and PGP longer than that, and I still think it's a pain in the ass. Whenever I'm configuring a new mail client, I have to fiddle with multiple settings just to get it to send encrypted mail.

There's a real opportunity to build something much, much simpler on top of PGP. All you really have to do is pick some sensible defaults and automate a few steps. Look at how many nerds can't be bothered with encrypted communication, let alone normal people.

Making GPG and programs that use it easier to use would be nice. But the primary issue is that many people that should be able to comprehend PKI basics and necessary background material to use it, are too "busy" or "lazy" to spend the limited time to even scratch the surface.

I face this daily, since I'm the go-to guy at my office for scripting/coding solutions for these folks. They just want it to work without having to learn or understand their decisions. And these are the same people that will spend hours figuring out complex lunch accounting issues or read volumes on video game strategies or rebuild engines.

I mostly agree, except there are some perils involved.

Bob has to make sure that the public key he thinks is Ann's really truly is Ann's, and not Eve's.

That would be a hard problem to solve.

You can do all that stuff, but it's the fact that you have to understand these concepts to use PGP that makes it difficult, not the way they're documented.

If you don't understand key management and public/private keys, signing, etc., you either have to depend on someone that does, or cargo-cult your way through using it. And it's not difficult given a little "want to". Alton Brown could teach the concepts in a single show.

I understand this stuff, and I believe I can teach it to my friends. But I don't believe I can convince my friends to put up with the software that is currently available. That is the entire reason I can't find anyone to use PGP with.