This dissertation provides research on alienation from learning in differential learning and developmental milieus (vgl. Baumert/Stanat/Watermann 2006) within the strongly stratified educational system of Luxembourg. Alienation from learning is defined as a student´s generalised negative orientation towards learning (Hascher/Hadjar 2018, S. 179) and collocates with severe consequences including school dropout (see Hascher/Hagenauer 2010, S. 220). The study focusses on the question of how the development of alienation from learning differs between the differential learning and developmental milieus within Luxembourgish secondary school tracks. The conceptual framework is based on the perspective of differential learning and developmental milieus (Baumert/Stanat/Watermann 2006), the theory of school culture (Helsper 2008; Kramer/Thiersch/Ziems 2015) and further culture sociological and resonance pedagogical approaches (Willis 1978; Beljan 2017). Combining research on school culture and research on school alienation, this works examines the interplay between school culture and individual students and its impact on alienation from learning. Conceptualized as a mixed method study, this research aims for a holistic picture on alienation from learning by combining quantitative and qualitative approaches. The quantitative part is based on a three-year panel study with students from all secondary school tracks (grade 7-9). Employing random effects models and growth curves models it investigated the degree and development of alienation from learning over time. Qualitative group discussions and interviews with classes (grade 7) and their teachers from the high-achieving and low-achieving school track (corresponding to grammar school and the lowest secondary school track) were conducted to research how schools´ specific demands contribute to alienation from learning. The method employed in the qualitative analysis was the sequence-analytical habitus reconstruction approach. Quantitative analysis reveals a moderate but increasing degree of alienation from learning in all secondary school tracks from grade 7 to 9. Therefore, alienation from learning develops similarly in all secondary school tracks. Students from the high-achieving ES-Track show the strongest degree of alienation from learning whereas students from the low-achieving Modulaire-Track show the lowest degree of alienation from learning. Qualitative analysis identifies the high-achieving and low-achieving secondary school tracks as differential learning and developmental milieus characterized by diverging educational demands and standards on the class level. Consequently, when students’ orientations conflict with the school´s demands and offers there is a high risk for them to develop alienation. Track-specific possibilities and risks were identified with regard to bonding and alienation. Strong achievement orientation, theoretical educational content and highly standardised educational settings may foster alienation from learning depending on the students´ individual competencies and orientations.