Objectives: This study examined the influences of parent-adolescent relationship quality and parental controlling behavior on cyberbullying perpetration among Korean middle school students, and whether cyberbullying victimization has a mediating effect in this relationship. Methods: The participants of this study were 423 students (192 boys, 231 girls) from five middle schools located in Seoul, Incheon, and Gyeong-gi area. To measure the research variables, Bullying/ Victimization Questionnaire (Campfield, 2008), Parental Monitoring Instrument (Y. Kim, 2012) and Korean version of the Inventory of Parent and Peer Attachment (Yoo, Park, & Hwang, 2010) were used. The data were analyzed by means of descriptive statistics, Pearson's correlation, and structural equation modeling. Results: The results of this study were as follows. First, a higher rate of cyberbullying perpetration was related to lower parent-adolescent relationship quality and higher parental controlling behavior, cyberbullying victimization, and internet use. Second, cyberbullying victimization mediated the effects of parent-adolescent relationship quality and parental controlling behavior on cyberbullying perpetration among Korean middle school students. Conclusions: The results of this study suggest that interventions for cyberbullying victims are important as well as parental role at home as a means to prevent or reduce cyberbullying perpetration among Korean middle school students.