Expanding populations, the impacts of climate change, availability of arable land, and availability of water for irrigation collectively strain the agricultural system. To keep pace and adapt to these challenges, food producers may adopt unsustainable practices that may ultimately intensify the strain. What is a course of technological evolution and adoption that can break this cycle? In this paper we explore a set of technologies and food production scenarios with a new, reduced-order model. First the model is developed. The model combines limitations in the sustainable water supply, agricultural productivity as a function of intensification, and rising food demands. Model inputs are derived from the literature and historical records. Monte Carlo simulation runs of the model are used to explore the potential of existing and future technologies to bring us ever closer to a more sustainable future instead of ever farther. This is the concept of a moving sustainability horizon (the year in the future where sustainability can be achieved with current technological progress if demand remains constant). The sustainability gap is the number of years between the present and the sustainability horizon. As demand increases, the sustainability horizon moves farther into the future. As technology improves and productivity increases, the sustainability horizon is closer to the present. Sustainability, therefore, is achieved when the sustainability horizon collides with the present, closing the sustainability gap to zero. We find one pathway for water management technology adoption and innovation that closes the sustainability gap within the reduced-order model’s outputs. In this scenario, micro-irrigation adoption, minimal climate change impacts, reduced food waste, and additional transformative innovations such as smart greenhouses and agrivoltaic systems are collectively needed. The model shows that, in the absence of these changes, and continuing along our current course, the productivity of the agricultural system would become insufficient in the decade following 2050.