As legal authorities consider the constitutionality of the laws surrounding prostitution in Canada, we have the opportunity to rethink some of the fundamental assumptions that have been made about sex work and the socio-legal responses to it. In this article we draw on the concept of structural stigma to analyze the stigmatic assumptions inherent in the Canadian laws and briefly describe their effect—the civic exclusion of sex workers. We then consider the ways in which these same assumptions of risk and immorality are reproduced in end-demand (partial criminalization), legalized (regulatory) models, and decriminalization. While the decriminalization of sex work is the response that relies on the least stigmatic assumptions, even the celebrated New Zealand model is not absent of moralization and “othering” discourse. Further reflection is required to conceptualize a policy approach that transcends stigmatic assumptions so as to respect the human and civil rights of sex workers.