This article discusses how student disengagement is conceptualized by English-speaking youth attending English urban public schools in Montreal, Quebec. School dropout is theorized as being a culminating event in a process of school disengagement (Rumberger, 2011). Using 2 qualitative methods (maps and interviews) in a grounded theory approach (Charmaz, 2014), a theory of disengagement is presented and supported by existing literature in student engagement and school dropout. Student disengagement is framed from a socio-ecological perspective (Lawson & Lawson, 2013) in a move away from its predominant conceptualization as an individual trait. In doing so, we highlight some issues of urban education in Montreal, addressing such themes as inequity, low-income status, experiences of failure and the pass/fail paradigm, the elementary/secondary school transition, normativity, and, finally, the public/private distinction in schooling.