Analyzing people’s decisions can reveal key variables that affect their behaviors. Despite the demonstrated utility of this approach, it has not been applied to livelihood decisions in the context of conservation initiatives. We used ethnographic decision modeling in combination with qualitative comparative analysis (QCA) to examine the herding decisions of Maasai households living near Tarangire National Park (TNP) during recent and historical droughts. The effects of the establishment of TNP on herding practices during drought were different than anticipated based on the size and reliability of several prominent resource areas that are now within the park. We found little evidence of people relying on these swamps and rivers for watering cattle during historical droughts; rather, these sites were more commonly used as grazing areas for small stock and wet-season grazing areas for cattle to avoid disease carried by calving wildebeest. Yet during the 2009 drought, many herders moved their livestock – especially cattle from outside of the study area – toward TNP in search of grazing. Our analysis of herding decisions demonstrates that resource-use decisions are complex and incorporate a variety of information beyond the size or reliability of a given resource area, including contextual factors (e.g., disease, conflict, grazing) and household factors (e.g., social capital, labor, herd size). More broadly, this research illustrates that pairing decision modeling with QCA is a structured approach to identifying these factors and understanding how opportunities, constraints, and perceptions influence how people respond to changes in resource access.