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This qualitative study investigates how Taiwanese high school students and teachers navigate cyberbullying within emotionally and institutionally constrained environments. Drawing on in-depth interviews, findings reveal normalized silence, peer surveillance, and teacher ambivalence, all reinforced by cultural norms and policy vagueness. Students' mistrust and fear of retaliation discourage disclosure, while educators face emotional labor and systemic inaction. Framed by intersectionality and trauma-informed theory, the study exposes how structural conditions sustain digital harm and silence. It calls for relational, emotionally responsive interventions that move beyond reactive discipline toward care-centered educational practice.