The field of positive education emerged as a growing arm of positive psychology which has attracted attention and critique. While these criticisms are valid, it is argued that positive education has more potential than critics suggest. Through a case study, it is claimed that positive education can positively impact students and teachers within the educational community. But success is not immediate. The case study describes wellbeing assessment and program evaluation between 2011-2017 in an all-boys Australian school. Analysing objective and subjective wellbeing and academic data from 2011 (n = 516), 2012 (n = 709) and 2016 (n = 934), the presentation will compare high performing students to lower performing students, based on average grades. Students at risk for lower academic, behavioural, and psychosocial outcomes benefited from the focus on wellbeing. High performing students were satisfied overall with life, reported feeling engaged with school, connected with peers, and saw themselves as being gritty, determined to achieve their goals. In contrast, lower performing students felt less engaged and connected. The assessments suggest that students have profited from positive education, with at-risk students benefiting most. The case study indicates successful positive education programs blend evidence-based learning from positive psychology and learning.