Unauthorized migration under global regimes of border and immigration enforcement has become more risky and costly than ever. Despite the increasing challenges of reaching, remaining in, and remitting from destination countries, scholarship exploring the implications of migration for agricultural and environmental change in migrant-sending regions has largely overlooked the prevalent experiences and consequences of “failed” migration. Drawing from recent fieldwork in Central America with deportees, this paper demonstrates how contemporary migration at times reverses the “channels” of agrarian change in migrant-sending regions: instead of driving remittance inflow and labor loss, migration under contemporary enforcement can result in debt and asset dispossession, increased vulnerability, and heightened labor exploitation. Diverse migration outcomes under expanded enforcement also reveal a need to move beyond the analytical binary that emphasizes differentiations between migrant and non-migrant groups while overlooking the profound socioeconomic unevenness experienced among migrants themselves. With grounding in critical agrarian studies, feminist geographies, and emerging political ecologies of migration, this paper argues that increased attention to the highly dynamic and diverse lived experiences of migration under expanded enforcement stands to enhance our understanding of the multiple ways in which contemporary out-migration shapes livelihoods and landscapes in migrant-sending regions.