In this paper, we draw upon data from a multi-year, ethnographic case study of a community-based organization in Detroit, Michigan to consider how the organization has used social media to influence reform discourse, educate local communities, and forward community-driven educational reform goals within an austere, neoliberal political climate. Our analysis is informed by critical race theory and critical literacy scholarship, and it offers implications for enacting citizenship and democratic educational change. It also reveals insights about the ways in which technologies and ever-changing modes of communication can influence communities' critical literacy and civic action. We aim to boost the limited attention paid to the use of social media in urban educational activism, leadership, and policy research.