This study explores working-class males' engagement with high school education as statistically this group are underachieving and the chosen city in the North-West of England has been highlighted as an area of particular concern. Questionnaires and semi-structured interviews were used in an attempt to establish which issues affected their engagement in school, allowing a critical insight into their attitudes towards education.\ud \ud Findings indicate that there are a range of factors causing the educational disengagement of working-class boys in the city, ranging from deprivation to the content of the curriculum. The combination of causes is complex and varies between individuals, although the most common obstacle seems to be relationships between teachers and participants, with the issue of ‘relate-ability’ particularly evident.