In the emergent field of positive education, studies have investigated the characteristics of successful positive education interventions (Waters Australian Educational and Developmental Psychologist, 28(2), 75-90, 2011). These characteristics include following a whole school approach, integrating positive psychology into traditional subjects, and adopting a wellbeing curriculum (Waters Australian Educational and Developmental Psychologist, 28(2), 75-90, 2011). However, schools are complex environments and education in real-life contexts is influenced by a multiplicity of factors (Halliday et al. Contemporary School Psychology, 2019). There are few implementation studies within positive education (Halliday et al. Contemporary School Psychology, 2019), and there are fewer implementation studies that examine the student experience of learning. This is an important oversight, as the core aim of education is to support learning (Killen 2005). Therefore this case study explored the student learning experience of ten senior students within a whole school positive education initiative in an all boys private school in New South Wales, Australia. Through the utility of semistructured focus group interviews this study found that active, meaningful learning experiences enabled successful implementation. Moreover, family, school ethos and academic culture were significant contextual factors that influenced student learning. These findings informed recommendations on how to improve the student learning experience within positive education initiatives.