This article examines the internal structure and dynamics of the coffee economy in two districts of the southern Mexican state of Chiapas during the presidency of Porfirio Díaz (1876–1911). In both Palenque, in the northern highlands, and Soconusco, on the Pacific coast, production was oriented to international markets, direct foreign investment was a key aspect of coffee plantation development, and workers were recruited by the payment of wage advances (enganche), which they were then expected to pay off by labouring on coffee plantations. Yet, despite these similarities, the social relations that characterised coffee production in the two districts differed considerably. This article analyses those differences by comparing and contrasting the demographic factors, processes of land privatisation and the relationship between foreign investors, the national regime and local elites that influenced the nature and purpose of debt peonage in each district.