The emergent Housing First model, focused on new means of rapid rehousing of the homeless, is popular in North America among policy makers and the mass media. Yet little has been written on the Housing First model's transferability to Canadian municipalities. This report documents, analyses and interprets Toronto's Streets to Homes (S2H) programme, using primary and secondary research including semi-structured key informant interviews. The report concludes with a brief consideration of the article's implications for leadership.