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Conservation tillage practices can bring benefits to agricultural sustainability. Accurate spatial and temporal resolved information of field-scale crop residue cover, which reflects tillage intensity, is highly valuable for evaluating the outcomes of government conservation programs and voluntary ecosystem service markets, as well as facilitating agroecosystem modeling to quantify cropland biogeochemical processes. Remote sensing has the potential to cost-effectively detect crop residue cover, however, existing regional-scale studies were limited by insufficient ground truth data, scale mismatch between coarse satellite pixels and ground data, and the lack of key spectral data for detecting crop residues. Therefore, this study developed an innovative cross-sensing framework to integrate proximal sensing, airborne hyperspectral imaging, and satellite Earth Observation through deep learning to quantify field-level crop residue cover fractions at the regional scale. Specifically, we have collected intensive ground orthographic photos and conducted airborne hyperspectral surveys at corn and soybean fields of Champaign and nearby counties in Illinois, the heartland of the U.S. Corn Belt. Through semi-automatic labeling aided by ResNet-50 and superpixel image segmentation, we obtained 6719 records of ground residue fractions. With these ground data, we developed the 1-dimensional convolution neural network (CNN) model using airborne hyperspectral reflectance, which has 0.5 m spatial resolution and 3–5 nm spectral resolution from 400 to 2400 nm, to predict residue fractions. By applying the CNN model to airborne pixels, we augmented "ground truth" data of crop residues and further combined them with Harmonized Landsat and Sentinel-2 (HLS) satellite data to quantify regional residue fractions at 30 m resolution. Results show that airborne hyperspectral imagery with CNN can accurately detect residue fractions (R2 = 0.82, relative RMSE = 11.73%) to effectively generate quasi "ground truth" data to support satellite upscaling to all fields. With independent ground data for testing, we found that the ground-airborne-satellite integrative framework achieved better predictions in estimating crop residue cover (R2 = 0.67, relative RMSE = 17.53%) than the conventional ground-satellite upscaling (R2 = 0.22, relative RMSE = 32.09%). We also found that the shortwave infrared wavelengths, particularly 2100–2300 nm, are vital for predicting crop residue cover. Sentinel-2 and Landsat-8 data have a comparable capability to track residue fractions due to similar shortwave infrared wavelengths. This study highlights the high accuracy of hyperspectral imaging to detect agroecosystem tillage management practices and the advantages of cross-scale sensing to cost-effectively integrate multi-source data to quantify field-level agroecosystem variables across scales. [Display omitted] • A scalable framework to detect field-level crop residue cover from sensing was developed. • Cross-scale framework integrates proximal, airborne, and satellite sensing to detect residue cover. • ResNet-50 and image segmentation facilitate efficient labeling of residue cover from field photos. • Airborne hyperspectral sensing can be deployed as "ground truth" collectors for tillage practices. • Shortwave infrared reflectance in Sentinel-2 and Landsat is vital to quantify crop residue cover. [ABSTRACT FROM AUTHOR]