Risk taking may be regarded as a normative behavior in adolescence. Risk-taking behaviors may include alcohol, smoking, drug use, delinquency, and acts of aggression. 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. The purpose of this study was to compare the risk-taking behavior of adolescents with learning disabilities (N = 307) and without learning disabilities (N = 307) over time. Specifically, this study investigated changes over time in adolescents' substance use, engagement in major and minor delinquency, acts of aggression, and gambling activities. Results indicated that, compared to their non-learning disabled peers, adolescents with learning disabilities engaged more frequently in some risk-taking behaviors including smoking, marijuana use, acts of delinquency, acts of aggression, and gambling. The results also indicate that for some risk-taking behaviors adolescents with and without learning disabilities differ in their trajectory of engagement. Implications of this study point to the importance of supporting adolescents with learning disabilities when they are faced with difficult decisions around risk taking.