In both the historic and modern eras, punitive responses to homelessness were largely based on negative stereotyping, profiling, and discrimination. Those who are homeless are wrongly portrayed as morally inferior, lazy, and dishonest individuals (the “moral depravation” discourse), blamed for their own misfortunes (the “choice” discourse), and are treated as criminals or potential serious offenders needing to be repressed and confined (the criminality discourse), rather than as equal citizens worthy of respect and consideration. These three sets of beliefs have little to do with homeless individuals’ actual circumstances, or reality. However, their prevalence has had important legal implications for social rights litigation, preventing a necessary debate about the complexity and the multi-factorial dimension of homelessness – a phenomenon rooted in various social, economic, and political causes. In this chapter, we suggest that a broader discussion of the origins of the moral depravation, choice and criminality discourses, and the consequences of these three discourses for homeless people and communities in terms of criminalization and exclusive practices, strongly support the recognition of homelessness as an analogous ground of discrimination under section 15 of the Canadian Charter of Rights and Freedoms, as well as claims to social and economic rights. We argue that, when it comes to homelessness or to other enumerated or analogous grounds of discrimination, the courts’ consideration of immutability in a section 15 analysis must include consideration of the complexity and embeddedness of the social structures and interactions at play.