Artists who are committed to social justice through their work must navigate a complex contemporary art world characterized by numerous political positions and aesthetic expectations. In this paper, Nato Thompson observes two overarching approaches taken by artists—strategic and tactical—that operate against a political and economical infrastructure. Thompson describes successful examples in both categories, including sustained place-based work; culturally engaged radical pedagogy; engaged museums; engaged academic institutions; and a variety of work that raises questions rather than resolving them. Among the organizations highlighted as doing strategic socially engaged art are the Center for Urban Pedagogy and the Queens Museum; their efforts are infrastructural and sustained in a place over time. Artists highlighted as working through tactical and often guerrilla-style forms of intervention include Critical Art Ensemble and its Free Range Grain project and Paul Ramirez Jonas’ Key to the City implemented in partnership with Creative Time.