Several studies conducted around the world confirm the presence of gambling in detention facilities. Based on interviews conducted with male inmates in three Canadian penitentiaries, the authors of this article studied the reasons to gamble or not gamble in detention. The inmates' relationships with gambling prior to their incarceration were taken into consideration, to explain notably the influence of context on the reasons why they do or do not gamble. For most inmates, gambling is a good recreational alternative to boredom; however, some use it also to socialize or even protect themselves indirectly. Even more interesting is the fact that, despite the presence of gambling addicts among the inmates interviewed, none of the reasons generally associated with pathological gambling was reported during the interviews to explain gambling in detention. These results reinforce the influence of contextual factors on pathological gambling problems. Anxiety-producing factors in gamblers' lives, an environment where gambling is too accessible, as well as solitary habits, are conducive to addiction. By reducing stressful elements, as well as the availability, variety and special effects of gambling games, prison would indirectly control inmates' compulsive gambling habits during their incarceration.