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Writing on the Amazon in the early twentieth century registered the expansion of the mobility grid and circulation of peoples through rubber extraction assemblages and the construction of the Madeira-Mamoré railroad. Socio-technical frontiers such as the Madeira-Mamoré railroad and posts in the Amazon were often described as spaces yet to be named and to find proper representation in narratives and maps, being simultaneously located within the frontiers of nation-states, and beyond mapped and demarcated territories. The chiasmatic relationship between Amazonian territory and representation gives rise to a particular conception of freedom as the possibility of movement through open space and across the nation-state’s limits. Engaging with the intersections between geophilosophy, literature, and law, this paper explores how the Amazonian environment was conceived as a nomos beyond the polis as the site of law-making in Euclides da Cunha’s essays in À Margem da History, written in lieu of the expedition with the “Comissão Mista de Reconhecimento” and Henry Tomlinson’s The Sea and the Jungle, a narrative account of his travels in 1909-1910. It is argued that while both authors celebrated the possibility of nomadic deliverance into Amazonian environments embodied by persons they encountered through their journeys, the reservations they express reveal pertinent ambivalences of technological and economic modernization. This paper suggests that while technological modernization enables modes of demarcation and codification of territories, the expansion of frontiers is perceived both as a necessary product of modernity, and as the very limiting element of its deployment as a predominant cultural-historical narrative.