Using a school-based sample of Washington, DC, fifth graders (mean age 10.38, SD = 0.66) and their parents (N = 408), we examined 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. Youths reporting signs of pubertal development were more likely to engage in these risk behaviors than students reporting no signs. Pubertal development was 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.