Uncertainty and context pose fundamental challenges in GIScience and geographic research. Geospatial data are imbued with errors (e.g., measurement and sampling) and various types of uncertainty that often obfuscate any understanding of the effects of contextual or environmental influences on human behaviors and experiences. These errors or uncertainties include those attributable to geospatial data measurement, model specifications, delineations of geographic context in space and time, and the use of different spatiotemporal scales and zonal schemes when analyzing the effects of environmental influences on human behaviors or experiences. In addition, emerging sources of geospatial big data – including smartphone data, data collected by GPS, and various types of wearable sensors (e.g. accelerometers and air pollutant monitors), volunteered geographic information, and/or location-based social media data (i.e., crowdsourced geographic information) – inevitably contain errors, and their quality cannot be fully controlled during their collection or production. Uncertainty and Context in GIScience and Geography: Challenges in the Era of Geospatial Big Data illustrates how cutting-edge research explores recent advances in this area, and will serve as a useful point of departure for GIScientists to conceive new approaches and solutions for addressing these challenges in future research. The seven core chapters in this book highlight many challenges and opportunities in addressing various issues of uncertainty and context in GIScience and geography, addressing different topics and approaches. The chapters in this book were originally published as a Special Issue of the International Journal of Geographical Information Science.