In this paper we present elements of a case study involving a Catholic boys' school in a large rural centre in Queensland, Australia. The study sought to identify philosophies and practices that might be interpreted as either enabling or constraining boys' educational outcomes. Given that positive and generative teacher-student relationships are positioned as central in improving educational outcomes, this paper focuses on relationship issues at the centre of boys' experiences of school. Here we present boys' desire for greater control and autonomy over their everyday school lives and their resentment with being controlled and constrained by their teachers' enactments of authoritative power relations. We look at how particular teacher assumptions might be associated with this resentment and discuss some of the implications of authoritative power relations in constraining boys' educational outcomes. Against this backdrop, and with the purpose of constructing more equitable and generative relations, we support the call for schools to develop professional learning communities so that they can explore how the socio-political dimensions of gender continue to be implicated in shaping and constraining relationships between teachers and students in their particular context