There is a growing body of interest in wellbeing across political, educational and social bodies in the UK. The thinking behind this is for human as well as economic reasons, to help people make more informed choices in their lives. There are suggestions to measure wellbeing more often and use that data to help government improve policies and enable companies and individuals to live more productive lives for example by considering being more altruistic to improve personal and family wellbeing during a time of financial austerity (O’Donnell, 2014: 9). There is a fundamental problem however in that there is no common understanding of what wellbeing is across different bodies and agencies, including education, mainly because the term is subjectively defined. Yet teachers are required to report to parents on children’s wellbeing and also safeguard their wellbeing, Teachers’ Standards 2012 (DfE, 2013), but there are no common measures of wellbeing in use nationally. The purpose of this case study is to try to reduce ambiguity about wellbeing issues through identifying gaps in knowledge in the literature about what wellbeing in schools is. The investigation uses qualitative methods and as an inside researcher, to aid authenticity of data, a two-tier approach to gathering data is taken within a constructivist paradigm. The approach enables three voices to be heard, that of pupils and parents (data set one) and then teachers (data set two). The first pupil theme revealed that pupils had a strong sense of connectedness to the school, friends and teachers while the second theme showed approaches to learning that had resonated with pupils. The theme to emerge from parents was a loving community where they felt enabled to entrust their children to teachers who were passionate about their role and evidenced compassion in their working with children. Themes from teachers revealed responsive and enthused professionals who, through collaboration in action learning sets, influenced transition arrangements and ways they felt they could be further empowered in their role. Wellbeing deriving from empowerment through interconnected relationships within and across the three groups leads to an analysis of the community as one that accepts difference. The significance of this for wellbeing in education and policy is discussed.