This study aimed to extend the limited knowledge on the motivational and identity aspects of youth at-risk in second chance programmes. The study examined the relationships between autonomy-supportive climate, adolescents’ sense of authenticity, and their dropout risk, as well as the mediating role that authenticity plays in the relationships, within the context of a second chance programme for at-risk youth. Participants were 181 students at-risk from Israel. Results from a multilevel path model analysis support the hypotheses. The findings indicate a positive correlation between autonomy-supportive climate and authenticity of students at risk. The analyses also revealed a negative individual-level relationship between authenticity of students at risk and their dropout risk, and a negative cross-level relationship between autonomy-supportive climate and students’ dropout risk. The effect of autonomy-supportive climate on students’ dropout risk was partly mediated by students’ authenticity. The present study extends the knowledge on the influence of autonomy-supportive climate on schooling by pointing out cross-level relations between this climate and youths’ authenticity, and by shedding light on the connection of these constructs with dropout risk. As this model of relationships is often reflected in the pedagogical rationale behind the design of second chance programmes for youths at risk, the study has important practical implications for administrators, teachers, and policymakers leading these programmes.