Drought is a natural part of the historical climate variability in the northern Rocky Mountains and high plains region of the United States. However, recent drought impacts and climate change projections have increased the need for a systematized way to document and understand drought in a manner that is meaningful to public land and resource managers. The purpose of this exploratory study was to characterize the ways in which some federal and tribal natural resource managers experienced and dealt with drought on lands managed by the U.S. Department of the Interior (DOI) and tribes in two case site examples (northwest Colorado and southwest South Dakota) that have experienced high drought exposure in the last two decades. The authors employed a social-ecological system framework, whereby key informant interviews and local and regional drought indicator data were used characterize the social and ecological factors that contribute to drought vulnerability and the ways in which drought onset, persistence, severity, and recovery impact management. Results indicated that local differences in the timing, decisions, and specific management targets defined within the local social-ecological natural resource contexts are critical to understanding drought impacts, vulnerabilities, and responses. These findings suggest that manager-defined social-ecological contexts are critically important to understand how drought is experienced across the landscape and the indices that are needed to inform adaptation and response strategies.