This talk examines why corporate sustainability initiatives intended to intensify smallholder cacao production and ‘spare land’ for nature conservation have failed to significantly increase smallholder yields, improve livelihoods, or slow the pace of land use and cover change. Rooted in a case study analysis from Southeast Sulawesi, Indonesia, I first draw on land use surveys, household surveys, and remotely sensed data (1972-2015) to show how most households (73%) in four study villages are transitioning away from cacao amid sustained declines in yields (-65.9%) and accelerating forest cover loss for non-cacao commodities. I then draw on long-term ethnographic research to discuss how cacao intensification initiatives have remained disconnected from the power and resource access relations now transforming smallholder livelihoods. These relations include low and volatile commodity prices, growing reliance on off-farm work, entrenched resource inequities, and intensifying agro-industrialization. I argue that cacao intensification initiatives fail because they render the problem overly ‘technical,’ narrowly framing the field of intervention around the smallholder and smallholder field. In so doing, they obscure the dynamics of supply chain concentration, land control, and uneven opportunity and change underlying contemporary livelihood shifts in rapidly transitioning agrarian economies throughout the Global South.