It has long been assumed that risk taking is closely associated with criminal behavior. One reason for placing criminals behind bars-aside from punishment and protecting the public-is to prevent them from engaging in further risky criminal activities. Limited attention has been paid to whether being inside or outside prison affects offenders' risk-taking behaviors and attitudes. We compared risk-taking behaviors and attitudes in five risk domains (ethical, financial, health/safety, recreational, social) among 75 incarcerated offenders (i.e., offenders who are currently in prison) and 45 ex-offenders (i.e., offenders who have just been released from prison). Ex-offenders reported higher likelihood of engaging in risky behavior, driven largely by a willingness to take more risks in the recreational and ethical domains. Benefits attributed to risk taking as well as risk perception did not differ between incarcerated and ex-offenders, indicating that the opportunity to take risks might underlie behavioral risk intentions. Our results also indicate that risk-taking activities are better predicted by the expected benefits rather than by risk perception, aside from the health/safety domain. These results highlight the importance of studying the person and the environment and examining risk taking in a number of content domains.