Social planning has remained a longstanding element of urban planning practice and continues to be pursued through different institutional structures in Canada. While the City of Winnipeg currently features no municipal social planning department, the City of Vancouver attempts to support its most disadvantaged neighbourhoods through its municipal sector. As these are two cities with high concentrations of Indigenous populations, this research uncovers the degree to which these two social planning models have worked to support the particular needs and interests of residents living in Winnipeg’s North End and Vancouver’s Downtown Eastside. Through the comparative case study of these two research sites, comprehensive document analysis and semi-structured interviews with key informants from planning agencies in each city, it is evident both models promote socially just and socially sustainable planning processes and outcomes within their respective neighbourhoods. However, neither is without fault. As a government body Vancouver is able to create and track progress in a more systemic way, setting targets and metrics for other government agencies, while information sharing and relationship building are where non-profit organizations in Winnipeg truly excel. This research explains how most non-profit organizations are unable to successfully sustain themselves, while municipal departments lack the rapport grassroots organizations more easily attain. Therefore, an integration of both models could begin to better support Canada’s most disadvantaged neighbourhoods with growing urban Indigenous populations.