This chapter focuses on the transition of middle years students from primary to secondary school. The authors examine the characteristics of students in this age group as a means for understanding what makes them more vulnerable to academic and wellbeing concerns during this transition period. The term middle years plunge is used to describe the disruption associated with their decline in academic achievement and wellbeing. The chapter identifies strategies and practices that can support middle years students during this time. The three-factor model proposed by Evangelou et al. is explained and activities for each aspect of the model are described. The authors identify specific groups of middle years students who may have unique struggles and increased vulnerabilities during transition to secondary school. These students include young people with disabilities, Indigenous students, and students from lower socioeconomic backgrounds. Accommodations for these groups of students are offered. A framework and audit tool for assisting school leaders in the processes related to effective transitions is explained and adjustments that facilitate positive transitions are discussed.