This study explores implications of a retention rate trend conundrum involving two first year student cohorts exposed to new and similar orientation and engagement initiatives within a health foundation year. The retention rate for one of the cohorts decreased by 10% in the past three years, whereas the retention rate for the second cohort increased by 15% over the same period. Additionally, the retention rate for the entire Health Group increased only marginally during the same period. The presented trends highlight the complexity of the task of designing effective orientation and engagement plans that meet the expectations, needs and wants of all students. For students who experienced a smooth transition, the most positive factors that helped with their transition in prioritised order include: academic resources provided for courses (e.g., lecture notes); sense of community; non-academic Mentor programs; and academic staff (e.g., quality of teaching and being approachable to ask questions).