Issues arising in the transition from secondary school to tertiary mathematics study are increasingly coming under scrutiny. In this paper, we analyse two practical aspects of the school–tertiary interface: teaching style; and assessment. We present some of the findings arising from a 2-year national project in New Zealand titled “Analysing the Transition from Secondary to Tertiary Education in Mathematics” supported by the New Zealand Ministry of Education. The results provide evidence of similarities and differences between teachers and lecturers in their preferred teaching approaches and assessment strategies that contribute to a transitional gap between the school and tertiary sectors. The results also show that each group lacks a clear understanding of the issues involved in the transition from the other’s perspective, and there is a need for improved communication between the two sectors.