The neighborhood context can interfere with parents' abilities to effectively monitor their children, but may be related to specific monitoring strategies in different ways. The present study examines the importance of mothers' perceptions of neighborhood disorganization for the specific monitoring strategies they use and how each of these strategies are related to youths' alcohol use and delinquency. The sample consists of 415 mother-child dyads recruited from urban and suburban communities in Western New York state. Youths were between 10 and 16 years of age (56% female), and were mostly Non-Hispanic White and African American (45.3 and 36.5%, respectively). Structural equation modeling shows that mothers who perceive greater neighborhood problems use more rule-setting strategies, but report lower levels of knowledge of their children's whereabouts. Knowledge of whereabouts is related to less youth alcohol use and delinquency through its association with lowered peer substance use, whereas rule-setting is unrelated to these outcomes. Thus, mothers who perceive greater problems in their neighborhoods use less effective monitoring strategies. Prevention programs could address parental monitoring needs based upon neighborhood differences, tailoring programs for different neighborhoods. Further, parents could be apprised of the limitations of rule-setting, particularly in the absence of monitoring their child's whereabouts.