In the emergent field of positive education, studies have investigated the characteristics of successful positive education interventions (Waters, 2011). These characteristics include following a whole school approach, integrating positive psychology into traditional subjects, and adopting a wellbeing curriculum (Waters, 2011). However, schools are complex environments and education in real-life contexts is influenced by a multiplicity of factors that cannot be controlled including location, safety, economic security, demographics, community and culture (Halliday et al., 2019a). Consideration of these contextual factors are vitally important as they determine the extent the positive education program is compatible with the needs of students (Halliday et al., 2019a). Moreover, there are few implementation studies within positive education (Halliday et al., 2019b), 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 semi-structured 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 and within positive education initiatives. In addition, the results of this study informed student and community centered curriculum design recommendations.