Winter cover crops are an essential part of managing nutrient and sediment losses from agricultural lands. Cover crops lessen sedimentation by reducing erosion, and the accumulation of nitrogen in aboveground biomass results in reduced nutrient runoff. Winter cover crops are planted in the fall and are usually terminated in early spring, making them susceptible to senescence, frost burn, and leaf yellowing due to wintertime conditions. In addition to remote sensing imagery, advances have been made in the use of proximal sensors integrated with GPS for on-field measurements, and the comparability of such measurements between platforms, as well as based on processing level is important. Cover crop growth on six fields planted to barley, rye, ryegrass, triticale or wheat was measured over the 2012-2013 winter growing season. There was a strong relationship between the Normalized Difference Vegetation Index (NDVI) and percent groundcover (r2 =0.93) suggesting that date restrictions effectively eliminate yellowing vegetation from analysis. The Triangular Vegetation Index (TVI) was most accurate in estimating high ranges of biomass (r2=0.86), while NDVI did not experience a clustering of values in the low and medium biomass ranges but saturated in the higher range (>1500 kg/ha). Accounting for index saturation, senescence, and frost burn on leaves can greatly increase the accuracy of estimates of percent groundcover and biomass for winter cover crops. Surface reflectance measurements were more correlated with proximal sensors compared to top of atmosphere, with intercepts closer to zero, regression slopes nearer to the 1 to 1 line, and less variance between measured values. NDVI was highly correlated with percent vegetative groundcover, though surface reflectance products did not necessarily improve the relationships. When the Scattering for Arbitrarily Inclined Leaves (SAIL) model was used with measured field variables reflective of realistic winter cover crop scenarios, there were not large differences between NDVI despite differences in residue cover and moisture. At low LAI, NDVI is not capable of differentiating between residue and vegetative cover.