In response to growing economic disparity in the City of Toronto, there has been a shift towards a community economic development approach in Toronto's most disadvantaged neighbourhoods, exemplified by the Toronto Strong Neighbourhoods Strategy (2005) and the Toronto Strong Neighbourhoods Strategy 2020. In addition to the City's efforts, a small community of foundations and nonprofits are also taking this approach. While community economic development has shifted the focus and social investment practices of these organizations, its impact is less clear. In this paper, I explore how nonprofits, foundations, and local government make decisions about how to make social investments to affect change in community economic development in Toronto's Neighbourhoods Improvements Areas (NIAs). On the basis of this analysis, I offer a series of recommendations to enhance decision making processes and evaluate the impact of these social investments on local economies in Toronto's NIAs.