This essay argues for the importance of Native literature’s insights to discussions of contemporary carceral conditions and, more importantly, the need for an indigenous feminist approach, one that sees the sexist and heteronormative impacts of settler colonialism as not only an outcome of, but also integral to, ongoing dispossession and neoliberal capitalist regimes of state and empire. While many scholarly discussions of carceral power leave little room for discussions of resistance, I argue both McNickle’s The Surrounded and Hale’s “Claire” imagine and articulate spaces and practices of freedom even though their texts are set in the most overtly assimilationist eras of the twentieth century: allotment and termination. In these spaces of freedom, for a fleeting moment, the protagonists are able to regroup, strategize, and simply “be indigenous,” shedding the shackles of the “criminal breed” or the uniform of the runaway ward. In ambiguous, if not pessimistic endings, both writers suggest that hope lies in the next generation’s ability to seize these moments, find these spaces, and reembody cultural practices of freedom that honor life and the land. Articulating an indigenous feminist analysis of carceral conditions in settler-colonial contexts, both texts thus see as an answer to those conditions an indigenous feminist resurgence that recenters kinship obligations and indigenous legal orders.