Many of the undernourished people on the planet obtain their entitlements to food via agricultural-based livelihood strategies, often on underperforming croplands and smallholdings. In this context, expanding cropland extent is not a viable strategy for smallholders to meet their food needs. Therefore, attention must shift to increasing productivity on existing plots and ensuring yield gaps do not widen. Thus, supporting smallholder farmers to sustainably increase the productivity of their lands is one part of a complex solution to realizing universal food security. However, the information (e.g., location and causes of cropland underperformance) required to support measures to close yield gaps in smallholder landscapes are often not available. This paper reviews the potential of crop phenology, observed from satellites carrying remote sensing sensors, to fill this information gap. It is suggested that on a theoretical level phenological approaches can reveal greater intra-cropland thematic detail, and increase the accuracy of crop extent maps and crop yield estimates. However, on a practical level the spatial mismatch between the resolution at which crop phenology can be estimated from satellite remote sensing data and the scale of yield variability in smallholder croplands inhibits its use in this context. Similarly, the spatial coverage of remote sensing-derived phenology offers potential for integration with ancillary spatial datasets to identify causes of yield gaps. To reflect the complexity of smallholder cropping systems requires ancillary datasets at fine spatial resolutions which, often, are not available. This further precludes the use of crop phenology in attempts to unpick the causes of yield gaps. Research agendas should focus on generating fine spatial resolution crop phenology, either via data fusion or through new sensors (e.g., Sentinel-2) in smallholder croplands. This has potential to transform the applied use of remote sensing in this context.