Thermal infrared (TIR) imagery is normally acquired at coarser pixel resolution than that of shortwave sensors on the same satellite platform and often the TIR resolution is not suitable for monitoring crop conditions of individual fields or the impacts of land cover changes that are at significantly finer spatial scales. Consequently, thermal sharpening techniques have been developed to sharpen TIR imagery to shortwave band pixel resolutions, which are often fine enough for field-scale applications. A classic thermal sharpening technique, TsHARP, uses a relationship between land surface temperature (LST) and Normalized Difference Vegetation Index (NDVI) developed empirically at the TIR pixel resolution and applied at the NDVI pixel resolution. However, recent studies show that unique relationships between temperature and NDVI may only exist for a limited class of landscapes, with mostly green vegetation and homogeneous air and soil conditions. To extend application of thermal sharpening to more complex conditions, a new data mining sharpener (DMS) technique is developed. The DMS approach builds regression trees between TIR band brightness temperatures and shortwave spectral reflectances based on intrinsic sample characteristics. A comparison of sharpening techniques applied over a rainfed agricultural area in central Iowa, an irrigated agricultural region in the Texas High Plains, and a heterogeneous naturally vegetated landscape in Alaska indicates that the DMS outperformed TsHARP in all cases. The artificial box-like patterns in LST generated by the TsHARP approach are greatly reduced using the DMS scheme, especially for areas containing irrigated crops, water bodies, thin clouds or terrain. While the DMS technique can provide fine resolution TIR imagery, there are limits to the sharpening ratios that can be reasonably implemented. Consequently, sharpening techniques cannot replace actual thermal band imagery at fine resolutions or missions that provide high quality thermal band imagery at high temporal and spatial resolution critical for many agricultural, land use and water resource management applications.