This paper proposes an overview of the development of oil palm production in Indonesia combining two levels: (i) a national and historical perspective of the development of the sector; (ii) a regional approach considering two contrasting provinces, Riau and Jambi. Starting with colonial times, the national approach deals first with the main periods that punctuate the development of oil palm plantations up to the contemporary period, marked by the liberalization of the economy. It emphasizes several factors that played a strategic role in the development of palm oil production, such as the role of the State and migration. After presenting the different models that structure the relationships among stakeholders and how these relationships have evolved, the role of small family planters is analyzed. This section ends with a review of some controversial issues: livelihood improvement, land tenure and customary rights, inclusion versus exclusion, market risks, forest and environmental threats and governance. The regional approach gives context to the development of palm oil production within two territories that have different historical backgrounds, with Jambi entering into production relatively recently. In each of the two provinces, the themes and issues involved in palm oil development identified at national level are analyzed, with specific emphasis on stakeholders’ strategic behaviours. The paper concludes with a comparative perspective on both provinces.