The impetus of this study was a concern for the education and general welfare of boys. The interest in boys’ education has grown notably over the past ten years. This interest is evident in media reports, popular psychology texts, education reports and scholarly writing. Academic research on boys’ experience of education is less prolific although it does include studies conducted by Australian and international researchers. Central to this commentary on boys’ education is the concept of masculinity. Here there is a strong claim that boys’ academic performance and behaviour is influenced by the way they construct and live out masculine expressions. This research study is situated in a Catholic secondary school for boys (referred to as the College) and seeks to illumine the school experiences of students at the school. As school Counsellor I noted that some boys were displaying a lack of motivation for learning, resisted independent thinking and seemed to be opposed to authority. These characteristics, in turn, contributed to diminished academic performance and troublesome classroom behaviour. This observation raised issues in respect to the boys’ perceptions of masculinity and the various expressions of masculinity within the school. An analysis of historical and contemporary documents identified a mismatch between the stated vision and mission of the school and the structural organization it creates. This mismatch pointed to a critical gap between the stated purpose of its education and the social reality of boys’ educational experience. This critical gap was particularly evident in the school’s commitment to educating boys within a social justice framework. It seemed that investigation into the gender regime of the school and the implications this has for students was warranted. A review of literature in respect to the concept of masculinity and boys’ education served to further clarify the research problem and the purpose of this study. This review identified the various contemporary understandings of masculinity. It also explored the current debate about what is happening to boys in education and provided an outline of particular elements of the social constructionist’s understanding of collective masculinity expressions within a school setting. Commentary on how a school can configure its particular gender regime was of particular interest to this study. This review identified three research questions to guide this study. These questions are: Research Question 1: How do the students of the College understand masculinity? Research Question 2: What is the College’s gender regime? Research Question 3: What are the implications for students of the College’s gender regime? This research study was informed by a pragmatic understanding of the epistemology of constructivism and the principles associated with the theoretical framework of symbolic interactionism. A two-stage research design of exploration and inspection was employed to aid data collection, analysis and interpretation. In the exploratory stage data was collected through a questionnaire to 255 of the 301 Year 12 cohort. These data were analysed using both quantitative and qualitative methods and the results gave direction to the type of data needed in the second stage of the study, the stage of inspection. In the stage of inspection, data were obtained through two processes, one-to-one interviews and focus group discussions. An analysis of data collected in the second stage of the study led to the identification of a number of key findings in the way boys understand masculinity and the school has organized its gender regime. These findings highlight the domination of playing sport and the subordination and marginalization of other masculine expressions. They also give evidence of the existence of a critical gap between the school’s stated purpose based on Christian values, justice, holistic development, respect for the dignity of the individual, human striving and so on, and the reality it produces. The study concludes by outlining a number of recommendations that suggest themselves for the future development of the College. It recommends that the school introduce a gender education programme for students, review the gender regime that supports playing sport as the dominant masculine expression, and provide structures and opportunity for other masculine expressions to find approval and acceptance. Finally it is recommended that the vision that the school holds for the education of boys and its structural organization be open to scrutiny and exploration in order that what the school holds to be most important in the education of boys will be intentionally pursued.