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.