I've been a long-term enthusiast of the The Tor Project. Whereas the Electronic Frontier Foundation covers the social and legal, Tor is perhaps the foremost technical organization keeping the Internet free and interesting.
Tor2web / OnionAccess
My active interest in Tor began in 2008 during a conversation with Aaron Swartz. Aaron told me about the wonders of hidden services and their potential for magic. We soon created Tor2web, a proxy service which makes hidden services accessible to the wider Internet. Tor2web received a little coverage, and overall was warmly received. I then funded a few patches to make Tor2web faster. Today Tor2web is maintained by the HERMES Center for Transparency and Digital Human Rights. I now operate OnionLink, the world's largest Tor2web portal.
In 2014, I was project lead (Technical Product Manager) of the Toroken project which aimed to add a cryptocurrency-based incentive for running a Tor relay. This was an extension of long stretch of research by Rob Jansen. In motivating the Toroken incentive, I also authored a Tor Tech Report charting the growth rates of Tor and how to improve them.
Modern Tor's Ineffectual Activism
To great sadness to me, modern Tor has migrated away from its more pragmatic past toward a puritan variant of activist culture. This culture, combined with generic paranoia, this results in a lot of circular firing squads.
This personality was always present within Tor, but it was only until 2014-16 that they standard wrestling control from the other factions. I could feel this growing change within the Tor community and it caused an immense amount of frustration. Even trying for over a year, forcefully bringing up the issue, I was unable to determine whether something as simple as the robots.txt exclusion standard was acceptable for darkweb search engines. As far as I could tell the verdict was, "If we feel we share the same mood affiliation, it's okay. Otherwise: never." I might go further to argue shared mood affiliation has become a general admissions test into Tor at all. I suppose this strategy is sensible if you really do vast networks of shadowy powers are out to get you, and there's turncoats at every corner, but it's immensely counter-productive for the long-term health of Tor as an organization.
I see these as symptoms of an ideology that prioritizes purity over efficacy. Unfortunately, these kinds of priorities make it very difficult to manneveur. I am reminded of this recent commentary on US-China relations from Yan Xuetong where its the ideologues on each side that are making the conflict worse.
This reminds me vaguely of Aaron Swartz. In our relationship, Aaron would have ethical clarity and say "We should do X." and propose a method of charging at the frontgate for achieving X. Upon which I would reply, "Charging the frontgate is unwise. Anyone entrenched is entrenched precisely because they know how to defend themselves." I would then propose a less confrontational path which would get Aaron 70-80% of what he wanted with ~10% of the risk. Then we'd usually opt for my strategy. I am reminded of this post by Linus Torvalds essentially arguing for something in the spirit to my more pragmatic style.
"A very smart senior kernel developer once told me over drinks in a bar in Germany many years ago, something along the lines of "A foolish man bangs on the outside trying to change a company, a wise and cunning man works from within the company, changing it from inside such that it never knew what happened."
If I were to guess the future, I think Tor will continue to be a powerful regional player in the United States and Europe---perhaps even entrenching this position. Yet, Tor will continue to have palpably poor traction elsewhere---which is a shame when they could reach globally if they could just get along with people and authorities who don't 100% share their views.