Drawing on data from a longitudinal study of at‐risk youth (n = 593), this article reports on the analysis of factors that enabled these youth to succeed at school. It considers the impact of three baseline factors (age, gender, ethnicity) and a number of time‐dynamic factors [positive school environment, additional educational support, positive peer and parent relationships, exclusion/expulsion from school, depression and externalising individual risk, as well as the involvement of a range of services (mental health, justice, welfare)] upon educational progress. Over time, the educational status of this group of youth deteriorated. Differences were observed for indigenous, older and male youth who had poorer outcomes on average. Positive peer groups and a positive school environment predicted better outcomes, while the use of harsh disciplinary practices such as expulsion was the strongest predictor of poorer educational outcomes and had a pervasive negative impact on all three educational progress measures. Formal services did not make an appreciable difference to educational outcomes, while the provision of additional educational support only contributed to keeping youth enrolled in educational programmes but did not appreciably improve their educational outcomes. Improving educational outcomes for at‐risk youth requires a pan‐system response, whereby schools reduce the use of expulsion and create a positive school climate, other professionals support schools to retain challenging students at school and the positive resources generated by pro‐social peer groups are harnessed.