This paper draws attention to a knowledge gap in leadership models regarding bullying, particularly cyberbullying, an emergent form of student harassment. Given that parents are suing schools for failing to protect victims of bullying, educators need guidance in addressing harassment and discriminatory discourse in popular youth culture. The focus is on three important considerations: (1) the need to avoid criminalizing children and adolescents; (2) the need to clarify educators' legal obligations to protect students from psychological harm; and (3) the need to delimit educators' legal obligations to sustain school environments that reduce bullying and create equal opportunities for learning. Improved law-related courses, grounded in compatible theories on leadership, social justice, and ethics of care, are recommended for education students. Educators who take courses in these disciplines show great promise in helping schools navigate the unprecedented dilemmas of technology and pluralism through ethical and legally defensible alternatives.