The present study investigated cross-sectionally, through a mediation model, the role of perceived school context-related factors (school connectedness, peer acceptance) and cyberbullying involvement (as victim/bully) in school adjustment of native and immigrant students in elementary and secondary education. Overall, 819 elementary (50.2% immigrants) and 750 secondary school students (49.1% immigrants) from randomly selected schools completed self-reported scales regarding the variables involved. The results showed that both male and female immigrant students reported lower school adjustment than their native peers in elementary and secondary education. Among immigrant students school adjustment was lower in elementary than in secondary schools. Perceived school connectedness and peer acceptance contributed directly and positively to different dimensions of native and immigrant students' school adjustment. For all participants, and primarily for native secondary school students, cyberbullying involvement (as victims/bullies) negatively mediated between the perceived school context-related factors and school adjustment. Differentiated underlying psychological mechanisms could be considered within prevention actions to strengthen students' school adjustment, based on students' native/immigrant cultural background and level of education.