This essay is an early ethnographic exploration of the Dark Web Social Network (DWSN), a social networking site only accessible to Web browsers equipped with The Onion Router. The central claim of this essay is that the DWSN is an experiment in power/freedom, an attempt to simultaneously trace, deploy, and overcome the historical conditions in which it finds itself: the generic constraints and affordances of social networking as they have been developed over the past decade by Facebook and Twitter, and the ideological constraints and affordances of public perceptions of the dark web, which hold that the dark web is useful for both taboo activities and freedom from state oppression. I trace the DWSN’s experiment with power/freedom through three practices: anonymous/social networking, the banning of child pornography, and the productive aspects of techno-elitism. I then use these practices to specify particular forms of power/freedom on the DWSN.