This study responds to recent calls for the revitalization of the Vygotskian radical legacy and the reclamation of critical uses of cultural-historical research through a retrospective analysis of two case studies. The first case study describes the development and application of a discourse-based formative intervention framework to reveal psychological processes associated with reimagining and enacting possible futures among early adolescent Black girls. The second presents the FutureMaking Learning Lab’s efforts to address racial injustice in school discipline and empower parents and school personnel to collectively envision a culturally responsive, inclusive school system. Importantly, these case studies represented epistemological, methodological, and axiological expansions of formative intervention methodology through efforts to amplify the voices of participants and leverage their experiential knowledge through interactive participation structures and researchers’ integration of critical theoretical lenses to devise and employ mediating artifacts. These, in turn, support participants’ transformative agency to criticize current practices, ideologies, and structures, and imagine possible futures