The goal of the current study was to examine the combined influence of positive reinforcement processes using a behavioral task measuring risk taking propensity (RTP) and negative reinforcement processes using a behavioral task measuring deficits in distress tolerance (DT) on a range of risk taking behaviors among early adolescents. Participants included a community sample of 230 early adolescents (aged 9–13) who completed two behavioral tasks assessing reinforcement processes as well as reported on past year risk behavior involvement as assessed by items from the Youth Risk Behavior Surveillance System at a baseline and a 1-year follow-up assessment. Data indicated that at the Wave 2 assessment, RTP was positively related to number of risk-taking behaviors in the past year but only for those with low DT, with this finding persisting after controlling for the significant influence of male gender and higher sensation seeking. Results of the present study highlight the importance of considering both positive and negative reinforcement processes in combination when investigating vulnerability factors for early risk behavior engagement in youth.