This qualitative study examines the risk of homelessness amongst recent immigrant and refugee populations in the Greater Toronto Area by analyzing the various barriers which hinder newcomer access to adequate and affordable housing. This study incorporates the framework of Anti-Oppressive Practice (AOP) to understand the oppression, marginalization, and exclusion that many recent immigrants and refugee claimants experience within Toronto’s housing and rental markets and subsequently, how this initiates their cycle of homelessness. The findings of this study are informed by two semi-structured, informal interviews with housing and settlement workers in order to provide a working insight onto the issues that are affecting their newcomer clients on a daily basis. This study identifies challenges within Toronto’s housing market and highlights solutions put forth by housing and settlement workers. Similarly, this study examines initiatives put forth by the municipal government to address the barriers to accessing adequate and affordable housing.