New research frameworks that simultaneously address production and environmental goals are required to identify promising sustainable intensification options in high-yielding cereal systems. Here we estimated potential changes in environmental footprint associated with crop management practices aimed at breaking the yield ceiling for rice production in Uruguay. Results from a regional survey were combined with field experiments to integrate impacts on productivity and sustainability at two different intensification levels (average-yielding and high-yielding). Survey results indicate that high-yielding farmers produced 14% more grain compare to the regional average (7900 kg ha−1), with 25% to 99% lower agrochemical contamination risk and similar nitrogen use efficiency and carbon footprint. In on-farm trials, the alternative management practices increased yield beyond that of high-yielding farmers by up to 7% in small plots (8 site-years) and 15% in field-scale comparisons (6 site-years), yet an ex post assessment of environmental indicators shows significant decline of resource use efficiencies and increased carbon footprint. Thus, yield gains were not able to compensate for increased environmental footprint, highlighting the challenge of advancing the dual goals of SI in production systems nearing the yield ceiling. This study provides a simple but powerful framework for advancing SI in mainstream cereal production systems based on cost-effective modifications to existing agronomic experiments.