The transition to secondary school can be a challenging period for adolescents. Although several questionnaires exist to measure transition-related concerns, there is a need to develop a comprehensive survey for assessing the knowledge and skills that adolescents require to adapt effectively to a new school. Thus, the purpose of this study was to develop and investigate the psychometric properties of a preliminary self-report tool (PSTRS) for identifying the presence or absence of factors that facilitate transition to secondary school and are important for adolescent understanding of well-being. The PSTRS was developed in a series of stages that involved a systematic review of the school transition literature, a review of psychometric scales, empirical data of adolescents' well-being conceptualizations, expert reviews, and a pilot study. Seventy-one items were compiled to collect information on 20 school, social, physical, psychological, and spiritual components. Cronbach's alpha for the survey was 0.943 in a sample of Year 8 NZ intermediate school students (N = 471). Test–retest reliability was 0.866 in a subsample of 121 participants. Single-measures ICCs of subscales ranged from 0.501 to 0.943. The PC analysis resulted in a three-component factor structure. The PSTRS and its subscales positively correlated with well-being and negatively correlated with anxiety. Overall, PSTRS appears to be a reliable and valid tool for determining adolescent readiness to transition to secondary school. PSTRS data may be useful for researchers, school professionals, psychologists, and policymakers to better understand positive school transitions. Implications for future research and practice are discussed.