Homelessness in Canada has been on the rise since the 1980s. In 2006, the United Nations Committee on Economic, Social and Cultural Rights made a number of recommendations for the federal, provincial and territorial governments of Canada to address homelessness and inadequate housing as a “national emergency”(United Nations, 2006). Research has repeatedly found that individuals with addictions and mental illnesses are overrepresented among those experiencing homelessness (Argintaru et al., 2013; Bharel et al., 2012; Draine, Salzer, Culhane & Hadley, 2002; Drake & Wallach, 1999; Forchuk, Csiernik & Jensen, 2011; Goering, Tolomiczenko, Sheldon, Boydell & Wasylenki, 2002; Hwang et al., 2013; Khandor et al., 2011), with approximately two-thirds to three-quarters of the homeless population experiencing mental health challenges. This chapter describes the evaluation of a municipal strategy which focused on the housing needs and health outcomes of individuals experiencing addiction, poor mental health and poverty.