The purpose of this qualitative research is to learn from the professional wisdom of practitioners involved in implementing school-based psychosocial support in conflict-affected contexts. Practitioners from four different International Non-governmental Organizations (INGO) working in three different contexts—the Congo Basin region, the South Asia region, and the Sudan region—reflect on the concepts and realities of the psychosocial support models that their organizations use. A common theme emerging from these interviews is that the approach to psychosocial support has the potential to do harm. The practitioners provide real examples of the ways in which harm may occur and their possible causes. These causes include the lack of a formal venue for critical reflection within their organizations, internal disagreements between Child Protection and Education departments, an aid architecture that can foster competition between INGOs for funding, and the lack of commitment or organizational capacity to valorize local knowledge. I conclude with considerations for INGOs to reduce the potential harm produced by school-based psychosocial support programs in conflict-affected contexts.