This dissertation examines a dramatic agricultural transformation that occurred in the heavily indigenous region of Miahuatlán, Oaxaca (Mexico), between 1780 and 1880. Located on the southern edge of Oaxaca’s Central Valleys and populated by indigenous family farmers and a small group of nonindigenous merchants and administrators, the district of Miahuatlán found itself at the center of production for two incredibly valuable agricultural commodities. The first half of my project (1780-1860) examines the decline and disintegration of Oaxaca’s once-vibrant cochineal economy, an economy based in small-scale family farming that emerged around two important Spanish colonial institutions: a mercantilist monopoly and a system of trade known as the repartimiento de mercancías. I explore how these two crucial colonial institutions became undone towards the end of the eighteenth century and consider the subsequent decline in monetary income for Oaxaca’s family farmers and merchants in the early years of independence. The second half of my project (1860-1880) then explores how southern Oaxaca became one of the leading centers of coffee cultivation in all of Mexico. Through the construction of a new Pacific port in the 1870s, the privatization of communal lands, and modest improvements in road networks, Miahuatlán underwent a significant economic transformation that involved medium- to large-scale coffee estates and new forms of contractual labor. This project seeks to revise long-standing interpretations of agrarian change in pre-Revolutionary Mexico. Towards the end of the nineteenth century, sustained economic growth and political stability in Mexico resulted in the growth of large-scale commercial agriculture, disrupting long-standing social relations in the countryside and the widespread communal landholding of indigenous communities. Historians have long argued these processes caused significant land loss and provoked many of the tensions at the heart of the Mexican Revolution of 1910. However, a closer look at economic growth in Oaxaca suggests that large-scale commercial agriculture did not always look the same or have the same consequences in different regions. In a place such as Oaxaca with a long history of semi-autonomous indigenous communities with strong peasant economies, large-scale commercial agriculture was far less disruptive, often mediated by previous forms of land use and labor recruitment. The case of Porfirian Oaxaca forces us to reconsider the processes and consequences of Latin America’s export boom between 1850 and 1930 (often deemed the “Second Conquest of Latin America”) and how this period shaped rural social relations.