The rapid and large-scale development of oil palm cultivation generates a series of questions to R&D about the sustainability of mono-cropping production systems. The poor climatic resilience of present palm oil cultivation systems is revealed when extreme drought occurs, with measurable consequences on productivity. The oil palm directly responds to water stress through changes in sex ratio and drop in fruit development and oil synthesis. Oil yields are indirectly hampered when thick haze due to bushfires affects the photosynthetic activity for months. Biodiversity losses linked to the expansion of plantations at the expenses of rainforests have multiple impacts on ecosystem functions inside and around the plantation, and on the resilience of such functions to changing rainfall patterns. This chapter discusses the adoption of innovative plantation designs for climate-smart palm oil production, based on tree intercropping (for timber, rubber, and fruits production, or rainforest restoration) and/or complex agroforestry systems. Such diversified systems are bringing improvements in terms of climatic and socio-economic resilience, when compared to monoculture-based plantations that have hardly changed for one century.