Though Benjamin and Adorno’s various engagements with mass media suggest many possibilities for constructing approaches to descriptive and prescriptive critique, they have remained underexplored in media theory. Taken together, Adorno and Benjamin’s often incompatible views on the social significance of technological mediation offer a powerful framework for critical analysis of the political economies of contemporary socio-technological systems and practices, including mass online education, and for addressing persistent forms of technological determinism.