Particularly in highly stratified educational systems, the transition from primary to secondary school involves a substantial alteration of school culture as students leave their familiar environment of primary school and encounter a fundamentally different, initially strange school context. The transition to a new secondary school culture is presumably one cause of students' increasing school alienation as the students face specific expectations from their secondary teachers. The main aim of this paper is to shed light on the association between the change in school culture represented by the teachers' image of the ideal student and school alienation in the educational context of Luxembourg. The methodology follows a qualitative approach: in-depth interviews and group discussions with teachers from primary and secondary schools were analysed applying a qualitative reconstructive approach. The results confirmed the importance of the transition for students' educational trajectories and indicated its challenges concerning the changes in demands and values students are expected to meet. Various risk and protective factors concerning the development of school alienation over the course of the transition were identified according to the specific demands of a single school's cultures.