Despite decades of funding and initiatives aimed at widening participation in Australian higher education, there has been little change in the overall demographic profile of universities. A major focus of this agenda has been on the aspirations of young people from disadvantaged backgrounds, whose interest in higher education has been seen as problematic and in need of ‘fixing’. Indeed, even though there is broad agreement among practitioners and academics about the need to move beyond simplistic notions of ‘raising aspirations’, working-class experiences and identities continue to be pathologised when research and equity interventions narrowly concentrate on perceived deficiencies in knowledge, information, and inspiration. In this paper, we explore why this agenda has ultimately failed to generate real change by examining both the taken-for-granted assumptions underlying widening participation and how inequalities are inadvertently enacted within and through schools. Drawing on data from a larger project investigating the formation of aspirations among school-aged students in New South Wales, we frame our analysis through a case study of one school, Westland Hills Secondary School, comprising interviews with students (n = 5), teachers (n = 2), and the principal. Westland Hills provides a powerful foundation for this investigation given that it serves an historically working-class community located in a ‘city fringe’ area, close to a major university which has embedded equity as a core institutional value. In light of the seemingly intractable challenge of widening participation, we approach our analysis through theoretical reflexivity, using Bourdieusian and Foucauldian lenses to bring to light a more nuanced picture of educational and wider social inequalities. First, we work with Bourdieu’s concepts of habitus and misrecognition to unpack the ‘unthinkingness’ of school practices, which we find actually work to mould and reinforce a vocationally-oriented trajectory, despite a professed commitment to “transformation” of school culture towards an academically-oriented institutional habitus. Second, we work with Foucault’s notions of ethics and governmentality to investigate the forms of subjectivity that are being encouraged or marginalised in the commitment to “transformation”, finding that students are being asked to bear the burden of change by transforming their working-class “minds” in ways which are both resisted and somewhat illusive. Weaving together these distinct theoretical layers of analysis, we argue that widening participation has failed because it ultimately serves as a diversion from the structural inequalities that are deeply embedded within, and being reproduced by, the education system.