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The current article reviews prospective and experimental research on the relation between self-esteem and perceptions of vulnerability. These studies demonstrate that individuals with high self-esteem who engage in risk behavior often utilize a variety of self-serving cognitive strategies that protect them from fully acknowledging their vulnerability to the potential negative consequences of their behavior; e.g., they minimize their estimates of personal risk and overestimate the prevalence of the risk behavior among their peers. The article also provides data on an additional self-serving cognitive strategy employed by adolescents with high self-esteem—alteration of perceptions of others’ reactions to their own risk behavior. Finally, the article reviews the emerging literature on the relation between these cognitive strategies and maladaptive health behavior, and proposes that whether these strategies are maladaptive depends on the nature of the threat and the availability of opportunities to engage in compensatory self-enhancement.