The Tufts University Prison Initiative of Tisch College (TUPIT) offers students transformative learning experiences through various volunteer opportunities, including TAships and participation in various programs. The purpose of this project is to examine how student involvement in TUPIT fosters personal and academic growth by developing civic engagement, empathy, and leadership skills. Our research aims to identify the multiple pathways through which students gain a deeper understanding of systemic inequalities and build a sense of purpose and community. Key takeaways for conference participants include insights into how programs like TUPIT not only positively impact incarcerated individuals but also transform the students involved, empowering them to create meaningful social change, cultivate hope, and deepen their commitment to justice.