The focus of this study included selected South Carolina public high school leaders' experiences in applying district cyberbullying policies. With the increase in technology use by students, what was school-based bullying has expanded into cyberbullying, the application of electronic devices to harass and intimidate other students. Given the potential for psychological damage to students who are bullied, federal, state, and local policy-makers seek means to decrease, if not eliminate, both bullying and cyberbullying. In our litigious society, parents on both sides of bullying incidents often explore legal options to protect their children's rights and obtain justice whether their children bully or victimized. School leaders face ambiguous options in meting out disciplinary consequences. This ambiguity makes it critical that leaders have effective problem-solving skills. The theoretical framework used in the study focused on cognitive aspects of school leader problem solving. In this study, I selected six public high school leaders, based upon a documentary analysis of their district policies and how closely these policies adhered to federally suggested criteria. Once selected, I used the Critical Incident Technique (CIT) to elicit experiences from the leaders about using their policies. In general, these school leaders reported using district policies as a foundation for handling cases. All six of the participants used their professional discretion about procedures, which included when to involve law enforcement; the importance of the legal ages of both those who cyberbully and those who are cyberbullied; the time and location of cyberbullying incidents; and processes of evidence collection. The evolving nature of technology, along with differences in schools' digital infrastructure, affected how some leaders approached cases and maintained or improved their technology knowledge. Lastly, school leaders voiced concerns about several areas of their participation in cyberbullying investigations, such as the viewing of nude pictures or sexual videos and collection of evidence from privately owned devices. While leaders worried that poorly resolved cases could lead to student self-harm or suicide, they also expressed anxiety over potential litigation. Thus, school disciplinarians must rely on their problem-solving acumen to address ambiguities with rapid technical change and the pervasive nature of cyberbullying. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]