Research in visual arts education is often focused on philosophical issues or broad concerns related to approaches to curriculum. In focusing on the everyday work of teaching, this article addresses a gap in the literature to report on collaborative research exploring the experiences of secondary visual arts teachers in regional New South Wales, Australia. Drawing on qualitative data gathered through a process of educational connoisseurship and educational criticism, discussion focuses on visual arts teaching as a particular professional practice that is complex, intricate, emergent and adaptive. In drawing on themes emerging from the research, examples of unplanned aspects of teachers’ work that disrupt linear logics about teaching practice are examined. The article concludes by raising issues for further consideration and research.