Our group plants and harvests multiple genotypes of common wheat, durum wheat, triticale, barley, and oats across production environments that span the state of California. A subset of these environments include managed drought and nitrogen stress gradients. From these experiments we measure and report a wide range of agronomic traits on an annual basis, including grain yield, grain quality, stress stability, disease reactions and other agronomic characteristics. We also produce and curate material for more in-depth analyses of end-use quality and explore underlying genotype x environmental patterns and associated sustainability outcomes in these data. In addition, we record crop phenotypes via multi-spectral canopy and leaf reflectance using drone and handheld devices and contribute to the collective know-how related to drone use in agricultural field trials, including developing open-source software for efficiently extracting and analyzing multi-spectral data. Further, we explore the potential for cropping system adaptation to environmental changes via simulation modeling and conduct experiments that simultaneously measure the productivity and ecosystem service outcomes from diverse crops and crop management systems.