School districts are often given the challenging task of addressing problematic online behaviors committed by students while simultaneously protecting themselves from civil liability by not overstepping their authority. This is difficult, because the law concerning these behaviors is ambiguous and continuously evolving, and little consensus has yet been reached regarding key constitutional and civil rights issues. In the present article, the authors aim to shed light on some of the critical legal questions faced by school administrators by first reviewing several legislative actions and court cases involving problematic offline and online student speech or expressions. Next, the authors analyze the dispositions and extract principles that can inform and direct prevention and response efforts by educators. They conclude by underscoring the challenges of balancing legal guidance with humane consideration of the context and consequences of cyberbullying victimization among youth. (Contains 2 notes.)