This article examines the findings of a research program that investigated primary school mathematics teaching by graduates of the teacher education program at the University of Technology Sydney. The research comprised two distinct studies, one examining the experiences of student teachers in our teacher education program and the other considering the experiences of our graduates once they began to teach. I focus on what I learnt from these studies, particularly on the second one that highlights dilemmas faced by teacher educators when preparing their students for the realities of the classroom. I discuss the overwhelming nature of the experience of the first year of teaching and argue for more support from teacher educators for helping their graduates in those early days of teaching.