alt Hacker NewsThere were (are? it's been a while) many PGP users on the various darkweb markets. It was great fun teaching people to use it and actually having a community to use it with.
It was pretty awkward to later emerge as the PGP expert at work. I was at that time a bit shy about explaining how I got so comfortable with it.
The fundamental idea of technology such as PGP is that the percentage of stuff worth finding for the authorities needs to be really low. Ie. an incredible amount of "legitimate" innocent traffic needs to be flowing through the technology.
Otherwise, anyone who is using it at all will get court ordered and then, with our current system, you just lose.
Tor solves this by making traffic entirely homogenous such that any "it could be anyone" and by making nodes extraordinarily easy to host (such that any nerd can just leave one running 24/7). Even so there are way too few nodes.
But PGP-over-email is way too metadata leaky, and if you're doing anything that actually has a threat model, you need PGP-over-email to be itself common.