This study aims to determine the role of parental mediation and anonymity towards the tendency of cyberbullying behavior of high school students. This research needs to be done because the tendency of cyberbullying among students is increasing lately. In this study parental mediation and anonymity are predicted to have an influence on cyberbullying tendencies. Therefore the hypothesis in this study is the parental mediation and anonymity can predict cyberbullying tendencies of high school students.The subjects of the study were the XI grade students of state and private high schools in Yogyakarta, as many as 159 students, ranging in age between 15 to 19 years, the research subjects were obtained by purposive sampling. Three scales were used in this study, namely the parent mediation scale, the anonymity scale, and the cyberbullying scale. Data analysis uses multiple regression. The results showed that parental mediation and the perception of anonymity had a role in cyberbullying behavior (F = 10.264; df = 2.156; p <0.01). The effective contribution of the two independent variables to the dependent variable is 11.6% with each variable contributing 5.83% to the parent mediation variable and 5.78% the perception variable on anonymity.