Cyber-bullying is a psychologically devastating form of social cruelty among adolescents. This paper reviews the current policy vacuum as it relates to the legal obligations and reasonable expectations of schools to monitor and supervise on-line discourse, while balancing student safety, education, and interaction in virtual space. The paper opens with a profile and conditions of cyber-bullying. A brief discussion of the institutional responses to cyber-bullying follows. Finally, emerging and established law is highlighted to provide guidelines that are more likely than arbitrary responses, to help schools reduce cyber-bullying through educational means that protect students and avoid litigation.