Risk-taking behavior includes alcohol and drug use, delinquency, acts of aggression, sexual activity, and so on. Many studies have explored the relationship between adolescents and risk-taking behavior; however, only a few studies have examined this link in adolescents with learning disabilities (LD) or attention-deficit/hyperactivity disorder (ADHD). The purpose of the present study was to address that limitation by comparing the risk-taking behavior of adolescents with LD (n = 230), with comorbid LD/ADHD (n = 92), and without LD or ADHD (n = 322) on their substance use, engagement in major and minor delinquency, acts of aggression, sexual activity, and gambling activities. The study also investigated whether psychosocial variables (e.g., well-being) may act as mediating variables that help explain between-group differences. Results suggest that it is a combination of the LD and the secondary psychosocial characteristics that explains why adolescents with LD and comorbid LD/ADHD more frequently engage in some risk-taking behavior. (Contains 2 tables.)