Three decades after their establishment, many smallholder oil palm plantations are overmatured and will require replanting soon. Replanting offers a unique opportunity to redesign plantations, close yield gaps, boost farm productivity, and secure livelihoods. However, replanting requires knowledge, inputs, and financing. If postponed or done sluggishly, replanting could further exacerbate existing socioeconomic and environmental challenges in smallholder oil palm cultivation. We collected literature relevant to the replanting of oil palm and created a narrative literature review to highlight the challenges that smallholders face during replanting. We identified access to inputs, finances, and knowledge as paramount challenges that might influence smallholders’ decisions about when, how, and what to replant. Barriers to successful smallholder replanting in Indonesia are a lack of knowledge on replanting and proper training, uneven access to high-quality seedlings, as well as uneven eligibility for public replanting funds. We finish the review with recommendations for policymakers and researchers on how to overcome the challenges replanting holds and emphasize the opportunities replanting offers.