Millions of small waterbodies are dispersed throughout the middle of the North American continent, and billions of dollars have been invested to conserve, restore, and manage these waterbodies in the 20th and 21st centuries. Small waterbody conservation has been supported by different stakeholders aiming at improving water quality, enhancing floodwater storage, and supporting migratory bird breeding habitat. Conservation agencies are using hydrological and biological monitoring, modeling, and mapping to adaptively manage small waterbodies in the face of stressors such as invasive species and climate change. As remote sensing estimates of small waterbody surface water extent have become easier to access, understanding the capabilities and limitations of using remote sensing, especially in areas lacking surface water monitoring, is important for conservation decision making. Here, we used in situ monitoring and process-based hydrological modeling to explore remote sensing accuracy, especially related to waterbody size, emergent aquatic vegetation cover, and climatic conditions. Overall, we found that the accuracy of satellite and aerial imagery surface water mapping approaches vastly decreased for waterbodies smaller than 2 ha. We also found emergent vegetation could be masking surface water in waterbodies larger than 2 ha and that accuracy of some remote sensing estimates may decrease during wetter climatic periods. These results indicate that sensors commonly used for surface water applications alone may not be able to accurately detect small waterbody surface water, which supports the need for combining monitoring and modeling to understand how small waterbodies may respond to future changes in climate and land use.