In recent years, the intersection of higher education, identity, and carceral systems has required scholars and practitioners to actively work to interrogate carceral logics in educational settings. As an urban education teacher preparation program, collaborating with a higher education in prison program, we understand that educational gatekeeping practices have excluded collective knowledges, thereby deciding what expertise looks and sounds like -- and who and where it comes from. In this paper, we present both the problems and possibilities of what it means to confront higher education practices and redefine success measures for educator preparation programs as well as higher education in prison initiatives. Using autoethnography, we interrogate interdependent phenomena in higher education -- the decolonization of teacher preparation pedagogy, the practices of engaging the voices of those most impacted and disabled by teachers and school practices, and the reparative process of urban education towards advancing research of higher education initiatives in prisons. [Note: The volume and issue (35, 4) shown in the citation on the PDF are incorrect. The correct volume and issue are 36, 1.]