Using a school-based sample of fifth graders (mean age = 10.38, SD = 0.66) and their parents (N = 408) from Washington, D.C., the authors examine associations of pubertal development with early adolescents’ sexual and nonsexual risk behaviors and their caregivers’ parenting behaviors and of these risk behaviors with parenting behaviors. Results indicate that youths reporting signs of pubertal development were more likely to engage in these risk behaviors than were students reporting no signs. Pubertal development is not related to parenting behaviors; however, parents of youths who reported multiple nonsexual risk behaviors reported more parent–child communication about sexual topics. These results highlight the need to begin risk prevention efforts early, prior to pubertal development. Research is needed to understand how parents can help youths better cope with pubertal development to avoid involvement in sexual and nonsexual risk behaviors.