In 2005, Toronto City Council adopted the Streets to Homes programme, based on the “Housing First” (HF) approach, as the centrepiece of the City’s strategy to address homelessness (City of Toronto, 2005). Under HF, a client is placed in permanent housing immediately, and then receives supports for concurrent issues, such as addiction and mental illness, that affect housing stability (Hwang et al, 2012). HF is being widely embraced by North American policymakers and academics, who applaud its utility in facilitating permanent housing retention (Waegemakers Schiff and Rook, 2012). However, critics argue that HF programmes facilitate the removal of marginalised populations from city centres and represents a retrenchment of front line emergency services, reflecting neoliberal governance and the regulation of space (Klowdasky, 2009; Willse, 2010). Both the heavy reliance of quantitative, medically-oriented measures employed by proponents of HF and the equally abstract arguments of its detractors fail to assess the implications of a city’s embrace of HF on the overall housing and homelessness policies and the regulation of space. The current study intends to overcome these gaps by presenting qualitative research conducted through interviews with City of Toronto officials, service providers, and other key informants. The initial research questions focused on why the decision to adopt Streets to Homes was made, and its impacts on service delivery and access to public space. However, the employ of grounded theory allowed for a more holistic understanding to emerge of how HF does not represent neoliberalism, but rather is hampered by it. In order for HF programmes to succeed, they must be supported by a robust supply of affordable housing and adequate income supports, as well as a great deal of attention being paid to the psychosocial issues that often accompany homelessness. A failure to have these supports in place results in continued extreme poverty and poor community integration for clients.