Transition is about change, and change comes with its challenges. School transitions are challenging events in students' educational paths, with possible negative effects on their development. The transition from middle school to high school is one of the most difficult, generating many school dropouts. Recovering from disrupted educational trajectories and early school leaving raises significant challenges in adult continuing education. The study aimed to identify the teachers' perspectives regarding the students' transition to high school, the difficulties and the support activities at their disposal. 1373 teachers from the West Romania responded online to Akos and Galassi questionnaire in June 2023. The results indicate that teachers perceive significant challenges in the transition to high school, especially in the academic and organisational dimensions. Rural support programmes focus more on participation in education away from home and supporting students and parents. Urban programmes emphasise academic support through study and organisation skills training sessions for students. The implemented support activities, in spite of being quite diverse, are not congruent enough with the perceived difficulties. To foster more successful transitions, the support activities should be more structured, implemented jointly by high schools and secondary schools, and customised according to the school and social context.