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Whilst much interest is focused on gender, and classroom-level influences such as and classroom composition and teaching style on achievement, attitudinal outcomes have not received the same attention. This paper focuses on alienation from learning as one sub-dimension of school alienation. School alienation is a relevant issue for all those engaged in supporting students to thrive and have positive outcomes, as it is related to learning and social behaviour, and eventually achievement. This explorative study considered how classroom gender composition and perceived teaching style affected the development of alienation from learning in primary and secondary schools. A multi-level analysis, based on quantitative longitudinal data gathered in Luxembourg, was undertaken. The database included information gathered during three consecutive waves (2016–2018) from 338 primary school students and 376 secondary school students. Our results indicate that the gender gap in alienation from learning was more pronounced in primary school. A student-centred supportive teaching style (classroom level) decreased alienation from learning in primary school for boys – closing the gender gap; that is to say, it did change the difference in alienation between girls and boys. In secondary school, only individual-level perceived teaching style was associated with alienation if teaching style was simultaneously considered on both individual and classroom level. A high proportion of male students in the classroom seemed to go along with a higher alienation among all students in secondary school. This exploratory study indicates that teaching style may be a crucial factor for the attitudes towards school of all students, suggesting that employing student-centred and supportive styles could help to prevent school alienation. [ABSTRACT FROM AUTHOR]