While many people enter student affairs to support students, the cost of caring may include compassion fatigue or secondary stress. Accordingly, our constructivist case study examined how a program that serves at-promise students contributes to and alleviates compassion fatigue among its staff members. Challenges included the large scope of programmatic work, silos, high rates of staff transition, and difficulty in drawing boundaries. Supports included developing a culture of support at the program and institutional levels, sharing resources, and mentorship.