Moving from primary school (Year 6) to the next stage in schooling (Year 7 intermediate or middle school) can provide challenges for students, teachers, and parents. A study was carried out to investigate these challenges with a focus on mathematics for 65 students from six different urban primary schools in New Zealand. Qualitative data were collected from school and teacher documents, questionnaires, and interviews pre- and post-transition. Attention was paid to classroom practices and curriculum continuity, students' preparedness for the transition, and the kinds of support provided for the students. Students experienced a change in the mathematics classroom from a task-orientated perspective to a performance-orientated perspective. There were commonalities and differences among the students, teachers, and parents about the transition process and in particular preparedness, support, and mathematical practices. (Contains 1 table and 1 footnote.)