Purpose: The purpose of this study was to determine the characteristics of African American nonresident fathers who engaged in parental monitoring and to assess the relationship between engaging in monitoring and race-related socialization with their preadolescent sons on their psychological well-being. We also examined the moderating influences of demographic factors on the effects of a parenting skills intervention for fathers. Methods: Data from the Fathers and Sons Program were used to examine the parenting behaviors and psychological well-being of 287 nonresident African American fathers of 8- to 12-year-old boys. Results: Fathers who were younger, had more education, engaged in race-related socialization, and were less depressed monitored their sons more. Parental monitoring explained additional variance in depressive symptoms, while race socialization was important for understanding personal mastery among fathers in unanticipated ways. Older fathers increased their race socialization behaviors most in the parenting skills intervention, while all fathers enhanced their monitoring ability. Applications: The findings suggest the significance of involving nonresident African American fathers more fully in their children's lives as a way to not only protect their children but also improve men's emotional well-being. The applications of our findings for social work and public health practice are discussed. (Contains 4 tables and 1 figure.)