The agricultural supply chain plays an important role in the increasing food loss and waste (FLW) due to different causes. However, this can be clearly seen in citrus products like orange as this fruit is subject to different and critical conditions of FLW especially at the farm where workers are a key factor. This paper contributes by proposing solutions to decrease orange loss before and during harvesting. Consequently, this would lead to boosting food security levels. A system dynamics model was built to simulate and compare the results to the current situation. In addition, the case farm was selected for the purpose of the data collection from Jordan. The proposed model enhanced sustainability performance in general since the number of workers required to cultivate the mature orange has been increased to 13 instead of 10 in the current scenario. Furthermore, farmers’ profit improved by 19.5% in comparison to the current scenario because the sold orange has been increased and consequently this impacted the amount of orange loss pre-cultivation and reduced to be 9.5 tons rather than 26.09 tons in the current scenario. Nevertheless, implementing the proposed model can lead to maximizing social and economic performance while maintaining the environmental impacts at a low level as the orange loss decreased significantly. Further research can be done in the direction of applying circular economy and reverse logistics into the orange supply chain to integrate orange by-products and waste into an innovative logistics network to reduce the consumption of limited natural resources.