Enset (Ensete ventricosum) is the traditional staple food of Sidama people who live in Rift Valley lowlands to highlands in southwest Ethiopia. Enset is drought resistant, but it matures slowly, requires substantial manure inputs from cattle, and intensive processing. Maize, introduced to Sidamaland in the mid-twentieth century, is common in midlands and lowlands. Maize matures rapidly and provides more kcal/kg than enset, but it is prone to failure in dry years and requires chemical fertilizer, which is subject to global market price fluctuations. We compare cultural ecology, productivity, failure, and resilience of enset and maize in 410 farms across four Sidama ecological zones. The risks and benefits of enset and maize are complexly associated with variable local environments. Enset offers drought-resistant produce that, with sufficient manure inputs, is adequate for subsistence in the wet highlands, but its performance is more variable elsewhere. Fertilized, maize yields larger harvests than enset, but vulnerability to rainfall and global processes create special challenges. Maize and enset appear to be in different adaptive cycle phases: maize grows quickly and maize farms rebounded from crop loss within four years. Only half of enset farms recovered within six years after crop failure, complicating farming decisions in an environment with tremendous localized variation. In general, the Sidama zone shows a pattern of regional diversity with local specialization for maize only, enset only, or mixed maize and enset cultivation. In some areas maize has become a preferred crop and food for younger people.