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Using the symbolism of what we consider to be a ‘Sisyphean continuum’, in this paper the Anglosphere countries of Canada, New Zealand, the United States, and Australia are grouped to strategically reveal the shared challenges Indigenous peoples encounter in racial-colonial education systems. Fittingly, parallels are drawn between the punitive loop the mythical figure Sisyphus was doomed to. For Indigenous peoples bound up in dominant educational spaces, the barrage of racial-colonial institutional tools and mechanisms, enduring racism and cultural assimilation, the absence of collective achievement, the lack of Indigenous representation (e.g. personnel or knowledge), in parallel with sustained inter-generational advocacy, aptly mirrors the exhaustive punitive loop of Sisyphus. Guided by theoretical bridges synergising Indigenous and Western qualitative research techniques, three commonly repeated challenges (1. Deficit thinking; 2. Institutions; 3. Curriculum) are the focus of this paper. These themes are drawn from a broader study that sought the wisdom of sixteen Indigenous experts from across the Anglosphere. Our paper’s findings recentre the cycling educational challenges Indigenous peoples encounter and draw attention to the urgent need to turn towards and embrace marginalised voices and knowledge paradigms. [ABSTRACT FROM AUTHOR]