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Adolescent involvement in risk behaviors is a concern that crosses geographical and cultural boundaries. Research has identified a number of factors that influence child behavior outcomes. This study explored the role of perceived neighborhood problems, parent-child relationships, and parental monitoring, as they relate to engagement in risk behaviors among a sample of 497 Bahamian early adolescents. Contrary to the hypothesized direction, results of the latent growth model showed an increase in perceived parental monitoring over the four-year period. Consistent with our hypotheses, adolescents who reported greater monitoring reported less involvement in sexual activity, less involvement in physical fights, and less alcohol consumption. Positive interactions between parent and child also significantly predicted the initial status and rate of change of parental monitoring.