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Māori and Pacific school leavers, who tend to be clustered in low-decile schools, are less likely than any other ethnic groups in New Zealand to begin degree-level studies, to succeed in their first year, and continue with their studies. This chapter will draw on the research findings from a prospective, longitudinal, qualitative study of student transition from secondary school to university (Madjar, McKinley, Deynzer, & van der Merwe, 2010). The study was an in-depth, longitudinal one with young people in transition, recruited in their last term of high school and followed to the end of their first semester. A sub-sample was followed until the end of their second year of university study. The chapter will discuss the critical importance of engagement, both academic and social, for student success in university environment. We will also explore the significance of connections with the students’ whānau (extended family) and community, and the peer connections and their impact on students’ experience of transition.