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This paper examines the intersection of the not-for-profit (NFP) sector and social movement unionism (SMU) in Canada and the United States. Trade unions, facing declining membership and constrained bargaining power, have increasingly turned to alliances with nonprofits to expand their reach and pursue social justice objectives. Drawing on comparative institutional frameworks, the chapter situates Canada’s charity/NPO distinction, Québec’s “économie sociale”, and the U.S. Internal Revue Code or IRC 501(c) system as key contexts shaping potential coalition strategies. Historical and contemporary case studies – including the Fight for $15 (U.S. and Ontario), teachers’ strikes (Los Angeles), and partnerships against austerity measures (Québec) – illustrate how nonprofit-union alliances extend the scope of collective action and can influence collective bargaining outcomes. Our secondary analysis highlights structural differences across jurisdictions, identifies the challenges of sustaining durable coalitions, and argues that NFP-union partnerships, under certain conditions, remain a viable path for advancing labour rights, social equity, and democratic participation.