The first Amazon rubber boom (1870–1912) represents a defining event in the history of the Amazon and a pivotal moment in the development of modern industry. This chapter traces, from a transnational perspective, some of the most significant Brazilian and Spanish American literary responses to the cultural, political, territorial, and environmental transformations brought on by rubber extraction in turn-of-the-century Amazonia. It also examines how the literature of the period reinterpreted major rubber-related international incidents, such as the Acre territorial dispute (1899–1903), the Putumayo scandal (1907–1914), and the rubber regime known as “La Funera” (1910–1921). The chapter situates the works of Euclides da Cunha (1866–1909), Alberto Rangel (1871–1945), José Eustasio Rivera (1888–1928), and César Uribe Piedrahita (1897–1951) within regional narrative traditions and in connection with later literary and cultural production related to the Amazon rubber boom.