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This study investigates how Taiwan’s 2024 amendment to its anti-bullying regulations affects the handling of teacher-to-student bullying in elementary schools. Using qualitative interviews with educators, administrators, and legal professionals, the research reveals both opportunities—such as improved procedural justice—and challenges, including administrative overload, rural capacity gaps, and inter-professional conflicts. Analyzed through the Conflicting Rationalities Theory, findings show that legal and educational rationalities often clash, leading to stress, inefficiencies, and fractured trust. The study recommends integrating educational values into policy, piloting reconciliation mechanisms, and enhancing cross-sector collaboration. It contributes theoretical insight and practical guidance for constructing school anti-bullying systems that are fair, flexible, and education-centered.