The visual arts has a long tradition of providing a space for artists to take up disruptive practices such a, challenging what is known, questioning and exploiting cultural codes, and providing alternative social practices. This chapter is interested in how visual arts students take up these disruptive possibilities within the complexity of secondary schools; a space historically characterised by hierarchal power, surveillance, and institutionalized structure. This chapter draws upon interviews with art teachers to examine the discourses surrounding their observations of ‘disruptive’ art created in their classrooms. In particular, the author focuses on the stories of two students who through their artwork explored and transgressed normalised notions of sexualities and bodies, which was signalled to be problematic within the school context by the teachers. This discussion explores how teachers, students, and the general school community respond and negotiate the tension and discomfort that can arise from ‘disruptive’ art.