In the last decade, Positive Education was introduced into the Australian education context, including within many Christian church schools, with the ambitious aims to bring the science of Positive Psychology to learning and teaching, and to facilitate the advent of a resilient, tenacious generation of youth embracing its best self. Notably, despite its claim to increase student wellbeing and accomplishment, emerging research into Positive Education suggests it is having less effective impact than originally intended (Street 2017 & White 2016). Given the potentially interrelated aims of both Positive Education and the Christian Education, this thesis seeks to understand and explore how these two paradigms potentially conflict, align and/or bolster one another within the daily life of school culture, teacher practice and pedagogy. Further, this thesis seeks to explore teachers’ perceptions of reality, personhood and purpose and to understand whether these might be strengthened, and more aligned with the Christian faith tradition through the adoption of Cooling’s “What If Learning” initiative. In seeking to contribute new knowledge to the fields of both Positive Education and Christian Education, the methodological strategies pursued in this thesis are based upon a qualitative study of cases within an Australian Christian church school, the principles of strategic integration and the recent tenets argued within the building evidence of Positive Education in Christian schools.