This study provides a new assessment of Merton’s anomie/strain theory and fills in several gaps in the literature. First, using the data from the sample of adolescents in an especially suitable and interesting setting, post-Soviet Ukraine, it investigates the applicability of the theory to this context and reveals that predictive powers of anomic strain may be influenced by larger sociocultural environments. Second, it evaluates the possibility of theoretical elaboration of Merton’s theory through identifying contingencies such as external constraints on behavior and finds limited support for moderating effects of perceptions of risks of sanctioning and social bonds on anomic strain–delinquency relationships. Finally, it confirms that additional clarifications of the concept of anomic strain may be promising.