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As children are spending more of lives in cohabiting parent families, it has become increasingly important to understand the implications of cohabitation for children's well-being. We use the National Longitudinal Study of Adolescent Health to determine whether adolescents in cohabiting parent stepfamilies fare as well as adolescents living in married parent stepfamilies and whether teens in unmarried mother cohabiting families fare better or worse than children living with unmarried single mothers. Adolescents living in cohabiting stepfamilies experience greater disadvantage than their peers living in married stepfamilies. Some of these differences in family structure can be explained by socioeconomic circumstances, but the effects of family structure on delinquency and PPVT cannot be explained by these factors. Generally, we find that teens living with unmarried mothers are not advantaged or disadvantaged by their mother's cohabitation, exceptions include delinquency and grades. Yet, all of these family structure differences among children living in unmarried mother families can be explained by mother’s marital history. These results have implications for our understanding of cohabitation, a family form that has received limited attention. Moreover, these findings may contribute to debates about the importance of marriage for children.