PURPOSE: To examine the relation between "sexting" (sending and sharing sexual photos online, via text messaging, and in person) with sexual risk behaviors and psychosocial challenge in adolescence. METHODS: Data were collected online between 2010 and 2011 with 3,715 randomly selected 13- to 18-year-old youth across the United States. RESULTS: Seven percent of youth reported sending or showing someone sexual pictures of themselves, in which they were nude or nearly nude, online, via text messaging, or in person, during the past year. Although females and older youth were more likely to share sexual photos than males and younger youth, the profile of psychosocial challenge and sexual behavior was similar for all youth. After adjusting for demographic characteristics, sharing sexual photos was associated with all types of sexual behaviors assessed (e.g., oral sex, vaginal sex) as well as some of the risky sexual behaviors examined-particularly having concurrent sexual partners and having more past-year sexual partners. Adolescents who shared sexual photos also were more likely to use substances and less likely to have high self-esteem than their demographically similar peers. CONCLUSIONS: Although the media has portrayed sexting as a problem caused by new technology, health professionals may be more effective by approaching it as an aspect of adolescent sexual development and exploration and, in some cases, risk-taking and psychosocial challenge.