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Used a sample of 207 single-parent families residing in 104 small, Midwestern communities to test hypotheses regarding the link between community context and adolescent conduct problems and psychological distress. For boys, community disadvantage had a direct affect on psychological distress, while it indirectly boosted the probability of conduct problems by disrupting parenting and increasing affiliation with deviant peers. Community disadvantage was unrelated to the deviant behavior or emotional well-being of girls. Proportion of single-parent households in the community had a direct effect on girls' conduct problems. It also contributed indirectly to girls' conduct problems by increasing the probability of involvement with deviant peers. Possible explanations for these gender differences are provided.