Adolescence is characterized by a surge in maladaptive risk-taking behaviors, but whether and how this relates to developmental changes in experience-based learning is largely unknown. In this preregistered study, we addressed this issue using a novel task that allowed us to separate the learning-driven optimization of risky choice behavior over time from overall risk-taking tendencies. Adolescents (12-17 years old) learned to dissociate advantageous from disadvantageous risky choices less well than adults (20-35 years old), and this impairment was stronger in early than mid-late adolescents. Computational modeling revealed that adolescents’ suboptimal performance was largely due to an inefficiency in core learning and choice processes. Specifically, adolescents used a simpler, suboptimal, expectation-updating process and a more stochastic choice policy. In addition, the modeling results suggested that adolescents, but not adults, overvalued the highest rewards. Finally, an exploratory latent-mixture model analysis indicated that a substantial proportion of the participants in each age group did not engage in experience-based learning but used a gambler’s fallacy strategy, stressing the importance of analyzing individual differences. Our results help understand why adolescents tend to make more, and more persistent, maladaptive risky decisions than adults when the values of these decisions have to be learned from experience.