Occupy Wall Street (OWS) is a massive protest movement calling for radical social change and an end to unbridled corruption. OWS emerged in September 2011 in New York with highly confrontational demonstrations against the Wall Street banks, and a small encampment in the city’s financial district. Within weeks, hundreds of local camps emerged throughout the U.S., along with ongoing series of vehement, decentralized protest actions. Much to the chagrin of the American political establishment, OWS operates as an elusive and flexible, “leaderless” organization, without a centralized authority or party affiliation, and uses occupation as a primary form of protest. This paper looks at the ways in which the movements’ leaderless organization and egalitarian social vision were/are deeply influenced by anarchist principles like anti-authoritarianism (anti-statism), anti-capitalism, direct action, and prefiguration. It then discusses attempts by Occupy camps, such as those in New York, Philadelphia, and Oakland, to repossess spaces, rights, and other forms of social wealth within different urban contexts. It analyzes how the Occupy camps, as well as innovations like the General Assemblies, spokescouncils, and social media formations, are transforming urban landscapes and creating new forms of social and political engagement based on anarchist praxis.