For decades, Mexico has been one of the major illegal opium poppy cultivation countries in the world. In 2017-2018 the price of the opium gum dropped abruptly to a historical low, causing a sudden collapse of production. We analyze the dynamics of rural land systems amid this price collapse through a multi-site approach in three neighboring municipalities in the Southern Highlands of the state of Oaxaca, Mexico. We use medium-scale spatial resolution satellite imagery for a quantitative assessment in a five-year period (2016-2020), complemented by secondary data and structured/semi-structured interviews with poppy growers and other key informants. Findings show that all three municipalities experienced pronounced declines in the areas of overall cultivated agricultural land immediately after the poppy price collapsed (2017-2018). However, there is a clear contrast among municipalities in how these areas recovered the following years (2019-2020). We identify three differentiating factors that explain this contrast in land-system trajectories: different levels of extreme poverty, livelihood diversification, and geographic isolation associated to (trans)national migration networks. These findings contribute to the analysis of the dynamic relationships among rural land systems, local resource management (including agrobiodiversity), and economic globalization involving illegal crop-commodity cultivation and migration, particularly in Latin America. Supplementary Information The online version contains supplementary material available at 10.1007/s10745-022-00388-4.