Background: Schools are often held responsible for preventing or addressing cyberbullying, yet little is known about school administrator perceptions of cyberbullying and the challenges they face in addressing this public health issue. Aims: The goal of this study is to examine school administrators' perceptions of the facilitators of cyberbullying and barriers to primary and secondary prevention strategies. Method: Public school administrators (N = 36) participated in in-depth interviews about bullying and discussed their experiences with cyberbullying and their perceptions of cyberbullying facilitators and barriers to prevention. Results: Three main themes arose from the analysis: (1) cyberbullying as a major challenge; (2) facilitators of cyberbullying and barriers to preventive action, including parents and technology; and (3) prevention efforts, including unclear jurisdiction for action, primary versus secondary prevention efforts, and technology attributes that facilitate school response to bullying. Discussion: Although administrators perceive cyberbullying as a major challenge facing their schools, they are often unsure about appropriate primary and secondary prevention efforts. Relationships with parents and police complicate response and prevention as schools attempt to navigate unclear jurisdiction. Additionally, technology presents a challenge to schools because it is seen as an enabler of cyberbullying, a facilitator of prevention, and a necessary part of education efforts. Conclusion: Lack of research on prevention strategies, parents' knowledge and attitudes, and confusion about responsibility for addressing cyberbullying are barriers to action. Findings suggest administrators could benefit from additional clarity on which strategies are most effective for primary prevention of cyberbullying, and that prevention strategies should proactively involve parents to promote effective collaboration with schools.