Agricultural systems based on annual crops provide a majority of human caloric needs, a large portion of fiber needs, and an increasing proportion of fuel needs. Annual crops, in general, have limited access to and high demand for nutrients and water, lead to soil and water degradation, require high fossil fuel energy inputs, and cause biodiversity losses. At the same time, growth in global human population, fossil fuel depletion, and climate change loom and will further exacerbate the negative effects of annual-based agriculture. Long-term global annual crop production is unlikely to be able to match human demands with the sustainable capacity of agricultural lands. In fact, the need for humans to extract and export large amounts of nutrients, particularly nitrogen, from large portions of our terrestrial landscapes without further degrading the ecosphere over long periods of time presents one of the largest challenges of this century. Thus, a fundamental transformation of agriculture is an important component in creating a sustainable global society. The persistence, nutrient use efficiency, and resilience that characterize many natural ecosystems make them potential models for agricultural sustainability. The integration of ecological principles will play a critical role in the design of truly sustainable future agroecosystems as well as in the crafting of effective governmental policies regarding agricultural regulation and support. Stimulated by the demise of cheap energy and fertilizer as well as unpredictable weather patterns, humans are on the cusp of a transition from extensive reliance on annual crops to a new generation of agricultural systems that will need to function more like natural ecosystems. The goal of our symposium is to examine what natural ecosystems have to offer as ecological benchmarks for sustainable agriculture and how those benchmarks might inform long-term governmental policy. The impetus of this symposium proposal is the vision for American agriculture over the next 50 years (in press at Conservation Biology, December 2008) by Nugent, Jackson, Christensen, and White. Nugent and colleagues elucidate a vision of what future agroecosystems should look like and the policy instruments needed to get there. In our symposium, we want to expand upon their vision by examining which specific ecological processes and properties inherent in natural ecosystems need to be carried over to a post-contemporary agriculture that does not rely on cheap fuel and fertilizer, is productive, is resilient, and maintains biodiversity.