Over 40% of the earth's land surface are drylands that are home to approximately 2.5 billion people. Livelihood sustainability in drylands is threatened by a complex and interrelated range of social, economic, political, and environmental changes that present significant challenges to researchers, policy makers, and, above all, rural land users. Dynamic ecological and environmental change models suggest that climate change induced drought events may push dryland systems to cross biophysical thresholds, causing a long-term drop in agricultural productivity. Therefore, research is needed to explore how development strategies and other socioeconomic changes help livelihoods become more resilient and robust at a time of growing climatic risk and uncertainty. As a result, the overarching goal of this special feature is to conduct a structured comparison of how livelihood systems in different dryland regions are affected by drought, thereby making methodological, empirical, and theoretical contributions to our understanding of how these types of social-ecological systems may be vulnerable to climate change. In introducing these issues, the purpose of this editorial is to provide an overview of the two main intellectual challenges of this work, namely: (1) how to conceptualize vulnerability to climate change in coupled social-ecological systems; and (2) the methodological challenges of anticipating trends in vulnerability in dynamic environments.