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Between 1684 and 1730, Indigenous communities in colonial Chiloé began to increasingly seek out the Spanish legal system in order to denounce Spanish abuses, advocate for their communal interests, and ultimately contest the norms and terms of the local colonial system. Far from subjecting themselves to a foreign system imposed on them, Indigenous communities creatively took advantage of the possibilities offered to them through litigation in order to build stronger communal positions and leverage their own strengths, in the process developing a unique politics of engagement with the Spanish colonial system. Chiloé—the Spanish empire’s southernmost possession in the Americas—was a remote and isolated outpost of colonial rule where Spanish officials consistently took advantage of the region’s borderlands character in order to subvert proper legal process. In spite of this, Chiloé’s Indigenous communities leveraged a series of adaptations to their local environmental conditions, in addition to place-based forms of knowledge, as a way of highlighting Spanish dependence on Indigenous labor and know-how, By contesting arbitrary Spanish colonial administration, Chiloé’s Indigenous communities asserted themselves as active participants in the co-constitution of a negotiated local colonial order.