This paper investigates the ways that teachers in one alternative school blur the boundaries of the political, personal, and philosophical in their efforts to re-engage marginalised and disenfranchised young people. The labours of the school staff at Harmony High offer an intriguing narrative of working both within and against the grain of policy mandates, curriculum narrowing, and the pervasive effects of neoliberalism. Through the physical and social spatiality, critical pedagogical and affective engagement of learners, new schooling assemblages might be formed. The work being done by teachers in alternative schooling contexts such as that of Harmony High--while situated, meaningful and deeply contextualised--offers hope for reconstituting mainstream education in more socially just ways that serve the needs and interests of everybody.