Youth risk-taking behaviors present important public health concerns due to their prevalence and potential adverse consequences, underscoring the need for research and prevention strategies to promote youth’s healthy development. The present research examined the relationship between parental psychological control and risk-taking behaviors via benefit perception among high school and college students in Taiwan. Using a cross-sectional design, the study surveyed 378 participants to assess maternal and paternal psychological control, benefit perception, and engagement in risk-taking behaviors. Results indicated no significant difference in psychological control or benefit perception between high school and college students. However, college students reported higher levels of risk-taking behaviors, such as risky driving, alcohol use, and unprotected sex. Both maternal and paternal psychological control positively correlated with benefit perception and risk-taking behaviors. Furthermore, benefit perception mediated the relationship between psychological control and risk-taking behavior among high school and college students. These findings suggested that parental psychological control indirectly influenced youth risk-taking by shaping their perceptions of the benefits of such behaviors. The study highlights the importance of promoting autonomy-supportive parenting to reduce risk-taking behaviors and advocates for programs that enhance decision-making skills among adolescents and emerging adults.