For many Pacific Islander (PI) people, the decision to migrate to a well-developed country is often associated with hopes for increased access to education, health and employment opportunities. Despite almost forty years of continuous migration, PI learners in Australia continue to achieve low educational outcomes, poor transitions to higher education and unsustainable employment. This study aimed to investigate patterns of engagement, achievement and transition of PI learners at the secondary school level, working with fourteen PI learners from Melbourne’s western metropolitan region. Using a case study methodology, the study investigated the impact of learners’ ‘lived in’ experiences on their educational trajectories. This methodology fitted well with the study’s aim to collect in-depth and rich data and utilise a narrative writing approach. Data was analysed using constant comparison methods and cross-case analysis to extract common themes which were then compared with relevant literature and the empirical data to identify common patterns of school engagement, achievement and post-school pathways of PI.