The timely and accurate quantification of grassland biomass is a prerequisite for sustainable grazing management. With advances in artificial intelligence, the launch of new satellites, and perceived efficiency gains in the time and cost of the quantification of remote methods, there has been growing interest in using satellite imagery and machine learning to quantify pastures at the field scale. Here, we systematically reviewed 214 journal articles published between 1991 to 2021 to determine how vegetation indices derived from satellite imagery impacted the type and quantification of pasture indicators. We reveal that previous studies have been limited by highly spatiotemporal satellite imagery and prognostic analytics. While the number of studies on pasture classification, degradation, productivity, and management has increased exponentially over the last five years, the majority of vegetation parameters have been derived from satellite imagery using simple linear regression approaches, which, as a corollary, often result in site-specific parameterization that become spurious when extrapolated to new sites or production systems. Few studies have successfully invoked machine learning as retrievals to understand the relationship between image patterns and accurately quantify the biophysical variables, although many studies have purported to do so. Satellite imagery has contributed to the ability to quantify pasture indicators but has faced the barrier of monitoring at the paddock/field scale (20 hectares or less) due to (1) low sensor (coarse pixel) resolution, (2) infrequent satellite passes, with visibility in many locations often constrained by cloud cover, and (3) the prohibitive cost of accessing fine-resolution imagery. These issues are perhaps a reflection of historical efforts, which have been directed at the continental or global scales, rather than at the field level. Indeed, we found less than 20 studies that quantified pasture biomass at pixel resolutions of less than 50 hectares. As such, the use of remote sensing technologies by agricultural practitioners has been relatively low compared with the adoption of physical agronomic interventions (such as ‘no-till’ practices). We contend that (1) considerable opportunity for advancement may lie in fusing optical and radar imagery or hybrid imagery through the combination of optical sensors, (2) there is a greater accessibility of satellite imagery for research, teaching, and education, and (3) developers who understand the value proposition of satellite imagery to end users will collectively fast track the advancement and uptake of remote sensing applications in agriculture.