Music education programs in juvenile detention centers can offer incarcerated youth outlets for creative expression and collaboration. Programs center hip-hop music as a culturally responsive and transformative means for students in detention centers to foster individual creativity, self-esteem, communication, and to support positive youth development. Although previous research has explored experiences of youth participants and preservice music teachers in these partnerships, no work has explored experiences of student volunteers. The purpose of this intrinsic case study, therefore, was to explore experiences of collegiate students volunteering in a hip-hop composition program for incarcerated youth. Participants in this study were ten college undergraduate volunteers from a variety of majors across campus. We completed initial semi-structured individual interviews in the fall of 2023, facilitated two focus groups with participants, and completed final interviews after the conclusion of programming in Spring 2024. Throughout the program, participants completed written reflections after sessions, and the researchers compiled field notes and written reflections throughout the year. Six themes emerged from the data analysis process: a) Music as Way to Connect, (b) Everyone Can Make Music, (c) Counter-Space for Joy, (d) Facilitator as Teacher and Learner, (e) Moments of Humanity in Inhumane System, and (f) Negotiating Dissonant Lives & Spaces. To guide our interpretation of volunteer experiences, we used a service-learning theoretical framework, in which experiences “incorporate the fundamental elements of service-learning, reflection and reciprocity” (Jacoby, 2014; p. 2). First, in terms of reflection, students deepened their knowledge of the carceral system through first-hand experiences, making personal connections with residents as peers and engaging with them in ways that offered moments of joy and humanity. They wrestled with moments of dissonance with other volunteers on their commutes back to campus, and struggled to reconcile the freedom of their daily lives against the confinements and restriction of the residents’ lives. Second, regarding reciprocity, volunteers engaged on the residents’ terms, entering the space as collaborators and facilitators rather than teachers, working with residents to tailor musical experiences that emphasized their own creativity and expression. A knowledge and love of hip-hop was critical for volunteers, as this shared musical knowledge helped break down initial barriers and create the conditions for residents to realize their musical talents. Findings point to a service-learning program that fostered the creativity of residents and volunteers alike, built on shared musical values and the opportunity to cultivate moments of humanity in the lives of incarcerated youth.