Drought is a complex challenge experienced in specific locations through diverse impacts, including ecological impacts. Different professionals involved in drought preparedness and response approach the problem from different points of view, which means they may or may not recognize ecological impacts. This study examines the extent to which interviewees perceive ecological drought in the Upper Missouri Headwaters basin in southwestern Montana. Through semistructured interviews, this research investigates individuals’ perceptions of drought by analyzing how they define drought, how they describe their roles related to drought, and the extent to which they emphasize ecological impacts of drought. Results suggest that while most interviewees have an integrated understanding of drought, they tend to emphasize either ecological or nonecological impacts of drought. This focus was termed their drought orientation. Next, the analysis considers how participants understand exposure to drought. Results indicate that participants view drought as a complex problem driven by both human and natural factors. Last, the paper explores understandings of the available solution space by examining interviewees’ views on adaptive capacity, particularly factors that facilitate or hinder the ability of the Upper Missouri Headwaters region to cope with drought. Participants emphasized that adaptive capacity is both helped and hindered by institutional, cultural, and economic factors, as well as by available information and past resource management practices. Understanding how interviewees perceive the challenges of drought can shape drought preparedness and response, allowing those designing programs to better align their efforts to the perceptions of their target audience.