Drawing on recent advances in the field of positive psychology, we present a multi-dimensional, whole school framework for measuring well-being within the school environment, organized around Seligman's (Flourish, 2011) PERMA model of flourishing. We apply this framework to assess student and staff well-being at an entire school-St. Peter's College, Adelaide, Australia. We report the student and staff baseline measurement strategy, present a snapshot of student and staff well-being, and test cross-sectional relations between the PERMA well-being pillars and physical health, job satisfaction, and organization commitment. 514 students and 143 staff completed a well-being questionnaire. Students with higher levels of optimism and happiness reported greater physical vitality. Staff with higher levels of meaning reported better physical health, and staff with higher levels of engagement and accomplishment reported greater job satisfaction and organizational commitment. By directly assessing subjective perspectives of well-being across multiple domains, and by incorporating both student and staff perspectives, there is potential to change the focus and conversation toward wellness promotion at all levels in the education system. © The Anglican Church of Australia Collegiate School of Saint Peter trading as St Peter’s College 2015. All rights reserved.