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Introduction: Early sexual activity and teen pregnancy are known risk factors for delinquency and justice involvement among male adolescents. However, less is known about these patterns among child welfare system (CWS)‐involved boys who face significant social barriers and past/current traumatic experiences. Methods: We prospectively examined these associations among male adolescents who identified as low and high risk for child‐maltreatment via a secondary data analysis of the Longitudinal Studies of Child Abuse and Neglect dataset—a large scale assessment of children, their parents, and their teachers in the United States to understand issues of child abuse and neglect. We extracted and examined data from 657 boys who were identified as at‐risk for maltreatment or with histories of substantiated maltreatment at ages 6, 8, 12, 14, and 16. We used structural equation modeling to examine the relationship between sexual activity (i.e., age of sexual debut, actively having sex, and sex resulting in a child) and changes in delinquency and justice involvement. Results: Male adolescents who have engaged in sex and/or have fathered a child had greater increases in delinquency over time compared to those who have not had sex. Further, fathering a child was significantly associated with justice involvement, especially for the high‐risk group. Conclusion: Results indicate that greater efforts should be taken to ascertain CWS‐involved male adolescents' sexual health practices and parenting status. Male adolescents in the CWS require support with accessing developmentally appropriate sexual health education and family services. [ABSTRACT FROM AUTHOR]