The interlocking challenges of racial injustice, economic disparities, and global pandemics brings renewed attention to the need for educators to scaffold effective responses to these crises with students. This paper moves away from examining how Transformative Learning (TL) can more deeply support transformations of these overlapping challenges, and instead considers what TL educators can learn from those who are engaging change on the frontlines of these crises. One of the most creative responses from communities who carry disproportionate harm from racial inequities centers the praxis of repair. This paper spotlights the importance of such repair work as a way educators who are informed by TL can support students’ responses to historic harms and related legacies of trauma. Our research draws from the rich theory and practice of Restorative Justice (RJ) and centers the mentoring process as a dynamic space to practice repair and accountability toward one another in ways that invite transformation. We suggest TL educators may utilize the intimate space of mentoring as a holding environment to support the often uncomfortable, provisional work of repair in ways that may support steps toward more equitable relationships and a more just world.