An accumulation of research has demonstrated that peers play a considerable role in older adolescent risk behavior engagement with risk taking often occurring in the presence of peers. Yet, questions remain about how peer influence manifests in the immediate context of risk behavior engagement and consequently whether the influence of peers has been overestimated. It is uncertain whether a situational effect takes place whereby the presence of the peers and/or their influence in that moment is key. Additionally, it is unclear whether certain adolescents are more or less susceptible to peer influence. To better understand the proposed influence of peers during risk-taking behavior, the current experimental study aimed to examine whether peers do act in a riskier manner in the presence of peers and further whether peer presence alone influences risk behavior or if a direct influence process is necessary. Further, the study aimed to examine potential moderators of peer influence. Utilizing a behavioral task assessing risk-taking behavior, 183 older adolescents (M age = 19.16, SD = .57, 63.9% female, 53.0% non-Hispanic White) came to the lab alone once and then were randomized to one of three conditions (alone, peers present, peers encouraging). If the target was randomized to peers present or peers encouraging conditions, the target brought in two, same-gender close friends for the second session. A repeated measures ANOVA with the within subject factor as the risk task score at each session and the between subjects factor as condition revealed a significant interaction of session by condition (F(2, 180) = 11.38, p = .001; partial eta-squared = .11) such that at the baseline session there were nominal differences between the three conditions but at the experimental session there was a significant increase in risk task scores particularly for the encouraging condition. None of the proposed moderators had a significant effect, suggesting that the experimental conditions had an equal effect across participants. These findings support the idea that older adolescents take more risks when being encouraged by peers but that the presence of peers on its own does not lead to more risks than when completing the task alone.