Conditional Cash Transfers are a type of welfare program in which recipients receive funds contingent on certain actions or involvement in activities. Governments and multilateral banks frame conditional Cash Transfers as an effective poverty alleviation strategy that provokes greater civic engagement in the Global South. Mexico’s Conditional Cash Transfer program,Oportunidades, includes an educational requirement for children. Studies ofOportunidadesfocus primarily on its impact on student enrollment, but lack research on the quality of education, retention and employment outcomes, and the impact on emigration. Drawing on three years of ethnographic research in a rural indigenous community in the Mexican state of Chiapas, I examine how teachers utilizeOportunidadesconditional requirements as a form of surveillance in the classroom. My findings reveal how emigration in La Gloria and its impact on student retention increases the vulnerability of teachers’ employment. These pressures unintentionally help shape how teachers perceive the program – as an intervention to an ongoing culture of migration. Finally, I discuss the impact that surveillance has in shaping educational and migratory aspirations among students and employment outcomes.