Research and public attention into boys’ education has increased in recent times among an emerging concern about the performance and retention of boys in schools. This concern, in many ways, constitutes a “moral panic” (Foster, Kimmel & Skelton, 2001, p.1) sometimes producing generalised and alarming statements such as ‘all boys are underachieving in school’ and are therefore becoming the “new disadvantaged” (Foster, et, al., 2001, p.7). Alongside these populist concerns about boys in schools generally, is an emerging body of contemporary academic studies into early school leaving, (Trent & Slade, 2001; Smyth, Hattam, Cannon, Edwards, Wilson & Wurst,. 2000; Smyth & Hattam, 2004) boys’ experiences of schooling, (Martino & Pallotta-Chiarolli, 2003), as well as some broader statistical evidence indicating a general decline in school retention rates in Australia since the early 1990s (Lamb, 1998). Performance in schools generally, and declining retention rates specifically, has been described as an “unacknowledged national crisis” (Smyth & Hattam, 2002, p.375). This study investigates boys’ education generally and early school leaving specifically, by focusing on boys who leave school before completing year 10. The study explores the stories, meanings and constructed experiences of a small sample (5) of young boys aged 14 – 16 years, who have left secondary school just prior to being interviewed. This is a qualitative critical ethnographic (L. Harvey, 1990) study located within a constructivist epistemology (Crotty, 1998). It aims to investigate early school leaving through narrative (Cortazzi, 1993; Way, 1997) and ethnographic inspired analysis (Robson, 2002) of transcribed interview data. Such analyses are referenced against a macro socio-political, economic, and cultural context characterised by changing global socio-economic and political circumstances, especially in regard to how these impact on schools and future possibilities for young people (Spierings, 2002). It seeks further understanding by drawing from a framework of concepts that invoke discussion of school culture, identity practices and how these are inferred (Smyth & Hattam, 2004), produced, understood and enacted within schools and social contexts. This study reveals that schools (as cultural and institutional practices) co-construct the often painful, lengthy and contradictory processes and experiences of early school leaving. Early school leaving therefore needs to be seen as an institutional and not merely personal or individual phenomenon. Appreciating the way schools assist in the process of early school leaving is important to understand, as it is within this domain that alternative educational practices can be located, constructed and enacted. It is hoped that this study will contribute to the current public policy debates on boys in schools, and as such be seen as an important contribution to public discourses and policy processes that help shape responses to boys in schools in general, and early school leaving in particular.