Despite evidence that the Canadian government’s attempt to deter prostitution, by criminalizing the behaviour that facilitates its occurrence, has been largely unsuccessful and detrimental to the safety and security of those who ‘sell sex’, members of parliament have done little to change course. Their commitment to a flawed paradoxical approach has forced many sex workers to provide their services in ways that increase their risk of being victimized. To date, there is little published research on how adult male sex workers understand and work around the law relating to sex work. In an effort to address this void, we present the views of 19 adult male escorts on two related issues: (1) the ambiguity of the criminal law relating to their trade and its enforcement; and (2) the use of strategies to cope with the dangers posed by the current legal climate. We show that although adult male escorts misunderstood the law, their comprehension of and experience with its enforcement gave them the impression that they must take precautionary measures to decrease their risk of being charged with a criminal offence and/or victimized by clients or the police.