Cyberbullying has been identified by school leaders and researchers as one of the most serious adverse consequences of incorporating information technology into the classroom. This article examines the legal status of cyberbullying by conducting an analysis of selected federal appellate court opinions. This analysis identifies a set of legal considerations that school leaders must attend to in confronting cyberbullying in order to protect students, teachers, and the interests of the school district. The article concludes with recommendations to district and school leaders before and during investigations of off-campus cyberbullying.