Schools are the most common site to implement evidence-based prevention programs and practices (EBPs) to improve behavioral and mental health outcomes among children and adolescents. Research has highlighted the critical role of school administrators in the adoption, implementation, and evaluation of such EBPs, focusing on the factors they should consider during the adoption decision and the behaviors needed for successful implementation. However, scholars have only recently begun to focus on the de-adoption or de-implementation of low-value programs and practices to make room for evidence-based alternatives. This study introduces escalation of commitment as a theoretical framework for understanding why school administrators may stick with ineffective programs and practices. Escalation of commitment is a robust decision-making bias in which people feel compelled to continue with a course of action even when performance indicators suggest it is not going well. Using grounded theory methodology, we conducted semi-structured interviews with 24 building- and district-level school administrators in the Midwestern United States. Results suggested that escalation of commitment occurs when administrators attribute the underlying causes of poor program performance not to the program itself but instead to issues related to implementation, leadership, or the limitations of the performance indicators themselves. We also identified a variety of psychological, organizational, and external determinants that accentuate administrators' continuance of ineffective prevention programs. Based on our findings, we highlight several contributions to theory and practice.