The conversion of grasslands to woodlands is an ecosystem transformation that threatens grassland biodiversity, the provision of important ecosystem services, and the sustainability of rural livelihoods. A global phenomenon, woody plant encroachment (WPE) has been particularly problematic in the Southern Great Plains of the United States where the actions of private landowners are integral to sustaining grasslands. Increased diversity in landowners’ motivations for owning land have shifted the social landscape of rural areas necessitating a better understanding of landowners’ perspectives about WPE and their subsequent management actions. Towards this purpose, I employed a mail survey to private landowners in the Edwards Plateau of Texas, Central Great Plains of Oklahoma, and Flint Hills of Kansas to investigate landowner perceptions and management responses to WPE. First, I assessed landowners’ acceptance of WPE as a function of how they relate to their land (i.e., sense of place), their beliefs about the positive and negative consequences of woody plants, and their perceived threat of grassland conversion. Then, I examined the drivers of landowners’ goal intentions to manage woody plants and their current use of five adaptive management practices that prevent WPE. My results demonstrate that landowners vary in their sensitivity to WPE based on how they feel connected to their land. This was true even though most landowners had low acceptance thresholds for WPE, believed it led to numerous negative outcomes, and perceived it as increasingly threatening at greater levels of encroachment. Most landowners wanted to control or remove woody plants and were actively engaged in management practices to do so. These findings address uncertainties about landowners’ acceptance of WPE and grassland conservation actions and provide broad implications for how people perceive and respond to ecosystem transformation.