There is widespread interest shown in the education of boys in school as evidenced in research, education initiatives and discussion in the general community. Research undertaken by Connell (1989, 1995, 1996, 2000), Laberge and Albert (1999), Mac an Ghaill (1994), Martino (1998), West (1999, 2002) and others suggests that there is a range of masculinities displayed by teenage boys. Some of the masculinities with which boys identify are in conflict with accepted ideas of educational achievement. This doctoral study investigates the contribution of teachers and school experiences to teenage boys’ understanding of masculinity. There are two components to the study. The first part is a systematic review of the literature to highlight findings about boys’ perceptions of relationships between masculinity and schooling. The second part is a qualitative empirical study of the views of a sample of Year 11 high school boys in two single sex Catholic schools. The interviews focus on their understandings of masculinity and their perceptions of influential aspects of school life. It includes an analysis of the boys' views of the impact of teachers, sport, discipline and classroom experiences. Participants in the study indicated that masculinity is changing and the community is requiring men to be more expressive of emotions. The majority of teenage boys interviewed stated that teachers and school experiences influenced their understanding of masculinity. Pupil - teacher relationships, conversations, exhortations and non-verbal communications are all perceived as means by which teachers influence students. Some teachers were regarded as good role models, making a positive contribution the boys’ masculinity. Interviewees reported that the schools promoted two masculinities, ‘sporting’ and ‘academic’. They spoke of contrasting interpretations of the appropriate expression of emotion. One finding of the study is that some of the teenage boys experienced a ‘spirituality of connected masculinity’ through singing, cheering and participation in school activities including sport, liturgies and retreats. Implications are drawn from the study and recommendations are made for improving the education of boys including how schools can encourage a diversity of ‘reflective’ masculinities rather than reinforcing ‘hegemonic’ understandings of masculinity.