The purpose of this research was to address the viability of a monoculture to polyculture agricultural land-cover transition within the context of the palm oil industry in Malaysia and Indonesia. A lifecycle assessment was used as a framework in the Cradle-to-Gate methodology used to understand sustainability hotspots, develop four future scenarios, and to measure three chosen indicators for metric changes. The four scenarios included a business-as-usual, perfect world, and two transition scenarios highlighting greenhouse gases, bio-control chemicals, fertilizer-use, and crop yield as indicators. In the four scenarios, a 1000 ha of plantation land with 140,000 palm oil trees created the backdrop for investigating nutrient cycling, cultivation methods, and the economic trade-offs of a transition. Primary literature was the main source of investigation and a wide-variety of current polyculture research helped create tangible data across the four scenarios. However, polyculture failed to address the socioeconomic barriers present in the governance, business-state, and regulations within this industry and region. An institutional analysis was conducted to investigate the political, financial, and regulatory barriers in this industry and recommend changes. It was concluded that while polyculture is an important form of environmental sustainability and can increase crop yield, the socioeconomic structure of the industry is the largest barrier to change and implement polyculture. In order for this social structure to change, it was recommended that the regulatory institutions, such as the Roundtable for Sustainable Palm Oil (RSPO), reframe their pressure points and instead focus on the interconnectedness of logging and palm oil companies with the regional governments.