Social skills and adaptability have been associated with a host of positive child outcomes. However, previous research has rarely examined the extent to which child symptomatology and family environment are associated with social skills and adaptability in children. Furthermore, no studies have looked at these associations longitudinally in preschool children with behavior problems, for whom social functioning may be especially important. The current study examined the relationship of five predictors (child oppositional defiant disorder (ODD), child attention-deficit hyperactivity disorder (ADHD), marital conflict strategies, parental depression, and parental warmth) with social skills and adaptability measured in preschoolers with behavior problems at age 3. The relationship was assessed concurrently, as it changed over time (controlling for initial starting point), and at age 6. One hundred sixty three children, mainly of European American and Puerto-Rican descent, were included. At age 3, ADHD, ODD, and maternal depression were associated with fewer social skills and lower adaptability. Paternal warmth and maternal positive conflict strategies were associated with higher social skills. Greater paternal positive conflict strategies were associated with greater improvement in social skills and adaptability from age 3 to 6. Paternal depression and paternal negative conflict strategies were associated with less improvement in adaptability. Paternal warmth was associated with greater improvement in social skills. At age 6, greater paternal positive conflict strategies were associated with higher social skills and adaptability. Maternal depression, paternal depression, and ODD were associated with lower social skills and adaptability. ADHD was associated with lower social skills and maternal negative conflict strategies were associated with lower adaptability. The findings shed light on how maternal factors, paternal factors, and child factors are related to the development of social skills and adaptability.