The odd thing about the Reality Winner deal is:

[politicat]

29. Just as a reality check - software for encryption is not that rare at all, and not illegal.

Spouse and I both have software that would enable us to reach dark web and make anonymized purchases (you do, too -- you have a browser. That's all you strictly need to get to the "dark web".). We both have Bitcoin accounts (we each bought one coin, long ago) and use PGP and secured browsers. I deal with HIPAA, Spouse deals with another form of privacy protected data. Encryption is necessary in our work. We both have a torrent client, because there's a reasonable amount of open source software that's released via legal torrent. We both have VPNs and TOR installed, because all free wifi comes with a high risk of a man in the middle attack.

I don't know the circumstances, I don't have nearly enough information, and I'm not sure I trust anyone who is talking because I don't know their motives, but let us not forget that having ziploc bags and a digital scale can be considered possession of drug paraphernalia, or indicative of someone who packs a diet conscious lunch.