This dissertation is a comparative ethnography of two groups of transnational soybean farmers in the Brazilian Cerrado. In this exploration of migration and industrial crop production for global markets, the new capacity for highly flexible farming is examined in relation to the fixity of family tradition, religious practices, landscapes, and expertise born of working the land. In 1968, Holdeman Mennonites embarked on a tour of rural Brazil. In search of autonomy from an encroaching cultural crisis, they found cheap farm land in Rio Verde, Goiás and encountered a government eager for their migration. Decades later, a group of Midwestern family farmers toured rural Brazil and found cheap, expansive land to occupy. They courted investors (mostly neighboring farmers), bought massive tracts of land, and settled in Luis Eduardo Magalhães, Bahia. The two groups’ migrations began with experiences of crisis: for the Mennonites a cultural crisis in the United States that threatened their family and community reproduction and for the Midwestern family farmers a farm crisis which threatened their livelihoods. In Brazil they adopted common farming techniques related to soil fertilization and tillage, yet differed in crop rotations, use of technology, and most starkly in their perceptions of what counted as “good farming.” Each community internally contested identity and value as they made meaning out of transnational lives and industrial farming. These cases problematize how we understand large-scale processes of the South American soy boom, the massive expansion of soy production in South America, the global land grab, and the proliferation of global land deals. This dissertation identifies difference and generativity of farming in two communities of transnational soybean farmers while also recognizing the power and domination behind such massive economic processes. The Holdeman Mennonite community pursues an alternative to soybean development in their use of family labor, avoidance of capital and technology, and diversified farming practices. The community of Midwestern family farmers adopts capitalist managerial and farming practices, yet reconcile this with their values of good farming. Together they reveal areas of convergence and divergence that make industrial, transnational soybean production possible.