North America’s midcontinent forest–prairie ecotone is currently exhibiting extensive eastern redcedar (ERC) (Juniperus virginiana L.) encroachment. Rapid expansion of ERC has major impacts on the species composition and forest structure within this region and suppresses previously dominant oak (Quercus) species. In Kansas, the growing-stock volume of ERC increased by 15,000% during 1965–2010. The overarching goal of this study was to evaluate the spatio-temporal dynamics of ERC in the forest–prairie ecotone of Kansas and understand its effects on deciduous forests. This was achieved through two specific objectives: (i) characterize an effective image classification approach to map ERC expansion, and (ii) assess ERC expansion between 1986 and 2017 in three study areas within the forest–prairie ecotone of Kansas, and especially expansion into deciduous forests. The analysis was based on satellite imagery acquired by Landsat TM and OLI sensors during 1986–2017. The use of multi-seasonal layer-stacks with a Support Vector Machine (SVM)-supervised classification was found to be the most effective approach to classify ERC distribution with high accuracy. The overall accuracies for the change maps generated for the three study areas ranged between 0.95 (95 CI: ±0.02) and 0.96 (±0.03). The total ERC cover increased in excess of 6000 acres in each study area during the 30-year period. The estimated percent increase of ERC cover was 139%, 539%, and 283% for the Tuttle Creek reservoir, Perry reservoir, and Bourbon County north study areas, respectively. This astounding rate of expansion had significant impacts on the deciduous forests where the conversion of deciduous woodlands to ERC, as a percentage of the total encroachment, were 48%, 56%, and 71%, for the Tuttle Creek reservoir, Perry reservoir, and Bourbon County north study areas, respectively. These results strongly affirm that control measures should be implemented immediately to restore the threatened deciduous woodlands of the region.