<p>This article draws on ten years of fieldwork and interviews with graduates of a non-profit pre-K-12 boarding school for poor lower-caste children in south India to explore how beneficiaries of educational philanthropy experience the expectation of “giving back” to society as a return on their education. In initial interviews, graduates confidently asserted that they would climb the corporate ladder at multinational firms and start-ups and one day lift their families out of poverty and transform society. Later, however, as they became fully reintegrated into their families and communities, they expressed cynicism and despair at the harsh realities that had mostly eluded them during their time living at the school and while staying in university dormitories. Paying down generational debt and beating back angry, sometimes violent loan sharks, while also navigating physical, mental, and substance abuse, especially among older generations—it was overwhelming. The expectation of “giving back” started to feel more like a burden that they could never relinquish rather than a civic duty they wanted or needed to fulfill. The paper analyzes the way graduates move through various emotional and psychological states in their perception of giving back before ultimately arriving at a more nuanced and compassionate understanding of their personal limits, if also the limits of the institution that raised them. Aside from offering one of the first longitudinal qualitative studies on the narrated experiences of educational philanthropy, the paper provides further insights into the challenges of extreme social mobility in societies marred by high rates of poverty and inequality.</p>