A lot of the comments I've been getting are in the genre of "well... but GPG works." Yes, GPG is a powerful tool that makes some encrypted communication possible . But is it really "working" if it's the tool we've had for the past 20 years, and we still ended up in a world where surveillance is so ubiquitous and privacy is so rare? Having used GPG, it seems more likely to me that there are only ~50k GPG users in the…
How's about this: rather than a protocol-up rewrite, how about just writing a library-up rewrite? Write a ground-up implementation of (maybe a subset of) RFC 4880, with opinionated choices of default ciphers (a bit like NaCl). Make it a portable library that can be used on all the popular mobile platforms and from all the popular languages. That's a plenty big enough job, and would fix the concrete pain points with GPG without throwing out the good part.
> We could try to slap a GUI on top of it, but I don't believe great products are made that way. Good UX requires thinking about interactions all the way down to the protocol.
What kind of concrete things would have to change at the protocol level? Plenty of good products conform to existing protocol standards, and a crypto protocol that has survived years of use in a hostile environment is worth its weight in gold. The talk of "modern" seems very handwavey as a reason to throw this out.
> GPG has such a small legacy install base (literally on the order of ~50k users), that there's no reason to maintain compatibility with OpenPGP.
I find it hard to believe there are only 50k users given that OpenPGP is built into the package-management infrastructure that every Debian user uses, and is required on Maven Central which virtually every Java system uses. Yes, these aren't people who actively chose it or are even aware that they're using OpenPGP - but protocols are like that; they're infrastructure.
And as for your 50k, that may be a small number but they're the people who really care about privacy. Snowden is among them. If you're trying to spread crypto, those are the last people you want to alienate.