Cyberbullying is a relatively new form of bullying, with both similarities and differences to traditional bullying. While earlier research has examined associations between school-contextual characteristics and traditional bullying, fewer studies have focused on the links to students’ involvement in cyberbullying behavior. The aim of the present study is to assess whether school-contextual conditions in terms of teachers’ ratings of the school leadership are associated with the occurrence of cyberbullying victimization and perpetration among students. The data are derived from two separate data collections performed in 2016: The Stockholm School Survey conducted among students in the second grade of upper secondary school (ages 17–18 years) in Stockholm municipality, and the Stockholm Teacher Survey which was carried out among teachers in the same schools. The data include information from 6067 students distributed across 58 schools, linked with school-contextual information based on reports from 1251 teachers. Cyberbullying victimization and perpetration are measured by students’ self-reports. Teachers’ ratings of the school leadership are captured by an index based on 10 items; the mean value of this index was aggregated to the school level. Results from binary logistic multilevel regression models show that high teacher ratings of the school leadership are associated with less cyberbullying victimization and perpetration. We conclude that a strong school leadership potentially prevents cyberbullying behavior among students.