In this special issue, the five previous articles trace the longstanding presence and integration of carceral practices in both K-12 and postsecondary education systems. As illuminated by the authors, carceral practices disproportionately criminalize students of color and impact pathways, trajectories, and how educational opportunities are experienced. In our review and closing comments for this special issue, we expand and share three emergent themes running throughout this volume: 1) Power Analysis, an investigation of macro systems and structures that determine specific contexts entrapping current and prospective students in the carceral system; 2) Worth/Value, an interrogation of the paradigms contributing to the devaluation, and ultimate criminalization, of Black and Latinx students within educational spaces; 3) Reform or Reimagine?, an inquiry and challenge on whether to advance with useful, but insufficient, changes to an unjust system or a move forward with new wide-sweeping and radical approaches to minimize damage to individuals. Our paper concludes with reimagining educational systems using these more radical approaches.