Recent developmental models assume a higher tendency to take risks in mid-adolescence, while the empirical evidence for this assumption is rather mixed. Most of the studies applied quite different tasks to measure risk-taking behavior and used a narrow age range. The main goal of the present study was to examine risk-taking behavior in four task settings, the Treasure Hunting Task (THT) in a gain and a loss domain, the Balloon Analogue Risk Task (BART) and the STOPLIGHT task. These task settings (...) differ in affective task moderators, like descriptive vs. experienced outcomes, anticipation of gains vs. losses, static vs. dynamic risk presentation and time pressure vs. no-time pressure and were applied in a sample of 187 participants from age 9 to 18. Beneath age trends, we were interested in their association with individual differences in approach behavior, venturesomeness, impulsivity and empathy above age, gender and fluid intelligence. Our findings revealed that risk-taking behavior is only low to moderately correlated between the four task contexts, suggesting that they capture different aspects of risk-taking behavior. Accordingly, a mid-adolescent peak in risk-propensity was only found under time pressure in the STOPLIGHT that was associated with higher impulsivity and empathy. In contrast, risky decisions decreased with increasing age in task settings, in which losses were anticipated (THT Loss), and this was associated with higher cognitive abilities. We found no age differences when gains were anticipated, neither in a static (THT Gain) nor in a dynamic task setting (BART). These findings clearly suggest the need to consider affective task moderators, as well as individual differences in temperament and cognitive abilities, in actual models about adolescent development. (shrink)