Background: Risks associated with teen sexting draw increasing concern from teachers and communities as developments in communication software and devices make sharing private content faster and simpler each year. We examined rates, recipients, and predictors of teen sexting to better plan education and preventative policies and strategies. A comprehensive literature review was conducted to determine the most likely predictors of teen sexting using prior survey studies and theoretical conceptions. Methods: We surveyed 314 high school students in an urban area of a large Midwestern city. Results: Males were found to more frequently report sexting. Impulsivity, frequency of electronic communication, peer pressure, peer sexting, and social learning significantly predicted sexting beyond age, race, and sex. Self-esteem did not moderate the effect of peer pressure to sext. Structural predictive models attained good fit to the data, and neither were moderated by sex. Conclusions: Sexting was highly associated with reported peer pressure, perceived norms, and impulsive decision making. Adolescents in relationships may be at particular risk of sexting. These findings will help parents, teens, and educators take appropriate measures to inform about and encourage the safe use of technology.