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This qualitative study explores high school counselors’ experiences with the SAFE Schools peer bullying prevention training. Through thematic analysis of 16 in-depth semi-structured interviews, we examine how counselors engaged with the training, implemented strategies in their schools, and navigated institutional and contextual barriers. Anchored in Guskey’s professional development model, ecological systems theory, and professional identity theory, findings illuminate affective and cognitive growth, systemic constraints, and variations in practice across socioeconomic and institutional settings. Findings from the study offer insights into the possibilities and limits of school-based bullying prevention from the perspective of frontline practitioners, concluding with participant-driven recommendations for systemic change.