While Canada has long criminalized aspects of sex work, the specific act of purchasing sexual services was not against the law per se. In 2014, however, the then Conservative government implemented new legislation targeting sex work clients. Given the criminalization and persistent stigmatization of their activities, assessing clients’ changing actions, perceptions, and knowledge of the new legislation is challenging. We thus turned to a major Canadian online sex work review forum to examine postings on forum threads. This paper examines the risk knowledge practices in which clients engage as they try to make sense of the modified legal regime and avoid new legal risks. Our findings illuminate clients’ varied understandings of their own criminalization.