Between 1870 and 1920, the department of the Soconusco in Chiapas, Mexico, became the country's largest exporter of coffee to global markets. The expansion of this economy required the mobilization of an ever larger workforce in the service of international commerce. Yet, as this article argues, global demand could only remake social and economic relations within the parameters of entrenched local structures. In the Soconusco, the development and endurance of incentivized contracts as opposed to coercive debt peonage were the result of tapping into a dispersed and diversified labor pool. By looking at the history of finca San Juan las Chicharras, this article explores both the day-to-day functioning of coffee plantations and the ways in which workers, planters, and politicians alike grappled with the redirection of their output toward ever more lucrative export production.