Bullying has long been a concern for students, parents, and schools. However, the explosion of communication technology has transformed the nature of bullying, allowing “cyberbullies” to extend their reach far beyond the physical schoolyard. This development creates uncertainty for schools, legislatures, and courts in assessing when and where schools should be permitted to regulate student behavior.

The growing number of tragic cyberbullying incidents, as well as national media coverage, has forced legislatures to take action. This has manifested itself in a number of different statutory forms and approaches. The most aggressive legislation appears to impose new duties on school districts and individual schools to police and prevent cyberbullying. Increased liability will likely accompany these new duties. This could be problematic since courts have been protective of students’ off-campus free speech rights when schools have acted aggressively to combat cyberbullying.

This Note argues that the potential for new liability that schools may face, while perhaps appropriate, will put schools in a “lose-lose” situation. Schools that choose to act in accordance with new legislation will undoubtedly face legal challenges by cyberbullies, claiming violations of free speech rights. Schools that hesitate to act may face liability for failing to fulfill their new statutory duties to protect victims of cyberbullying. In order to balance these competing interests, courts should apply existing legal standards more deferentially to allow schools to combat cyberbullying effectively while also respecting the First Amendment.