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It is only in the last few decades that Canadian trade unions have expressed labour solidarity with Indigenous peoples by bringing their attention to the distinct concerns of Indigenous workers in the workplace and beyond it. Trade unions have taken important steps to express support for their Indigenous members and their communities, yet little is understood about Indigenous peoples’ experiences in the capitalist labour market shaped by land dispossession, the ongoing manifestations of settler-colonial oppression, and the systemic economic marginalization by Canadian institutions and employers. It is pertinent to identify what unions are doing to support them and where they can strengthen labour solidarity so that they can develop critical sites of resistance against colonial-capitalist power. A closer analysis is needed to understand Indigenous peoples’ relationships to unions, relations between Indigenous and non-Indigenous working people, and the challenges for unions to build united struggles with Indigenous peoples. This study examines the spaces of union engagement with Indigenous workers and their communities amongst the challenges presented by the reality of ongoing colonial oppression in Canada. The purpose of this study is twofold: 1) to examine the roles that trade unions have had with Indigenous peoples in the paid labour market and recent initiatives that they have taken to meet the needs of Indigenous workers and unionists, and 2) to analyze the ways trade unionists understand and approach Indigenous peoples’ concerns and anti-colonial struggles within the broader confines of settler-colonial capitalism, and to determine the challenges to transforming their practices of solidarity with Indigenous peoples. This study draws upon semi-structured, indepth interviews with 22 Indigenous and non-Indigenous key informants who are elected trade union officials, staff, and rank-and-file unionists. The study’s findings reveal emerging activism of Indigenous workers within their workplaces, unions, and beyond, and the complexities between Indigenous peoples’ relationships with paid labour, unions, and struggles for selfdetermination. I argue that unions are turning their attention to support the distinct needs of Indigenous workers and to support anti-colonial struggles, but they are limited to redressing the effects of settler-colonial capitalism. They face difficulty engaging in solidarity due to the structural limitations of settler-colonial capitalism. By reflecting on participant insights into these challenges, this study proposes an anti-colonial framework for unionists to transform their practices of labour solidarity.