Immigration is challenging for youth as it requires reorganization of their developmental system and can increase their vulnerability to risk factors. Adaptation processes may be affected further by the cultural context in which they take place. This study explored immigration and adaptation experiences among youth at risk, who had immigrated to Israel from France and from the Former Soviet Union (FSU), and the impact of these experiences on the youth’s involvement in risk behaviors. The 27 participants interviewed for this qualitative study were 11 immigrant youth from France, 10 from the FSU, and 6 practitioners who work with immigrant youth at risk. Data analysis indicates that immigration is a significant life event that affects all spheres of the youth’s lives: identity, relationships with parents and peers, and school integration. Based on the participants’ interviews, we conceptualized adaptation as a multilevel process, related to youth’s potential involvement in risk behaviors. Moreover, immigrant youth’s experiences on different levels are shaped by their culture of origin—a matrix in which their adaptation and risk behavior occur. The findings, derived from a comprehensive perspective of both the youth and the practitioners, have substantial implications for practice and policy to enhance immigrant youth’s constructive adaptation. Specifically, we emphasize the key role of pre- and post-migration preparation that targets immigrant youth and their parents, and Israeli education institutions that receive immigrants.