Despite progress on many fronts, the number of people becoming homeless in Canadian cities was not declining. As a consequence, there has been a discernable shift in municipal responses to homelessness in recent years. Inspired by policy innovations in the United States, a number of cities are now implementing 10-Year Plans to End Homelessness, incorporating elements of “Housing First” into policy and program design and new system-level initiatives. In this policy landscape, the Research Alliance for Canadian Homelessness, Housing and Health (REACH3) sought to examine and evaluate the degree to which municipal and community-based plans are making progress towards ending homelessness and identify the factors that facilitate or impede plan success in cities across Canada.