The uncertain geographic context problem (UGCoP), first articulated by Kwan (2012; The uncertain geographic context problem. Annals of the Association of American Geographers, 102 (5), 958–968), refers to the problem that findings about the effects of area-based contextual variables on individual behaviors or outcomes may be affected by how contextual units (e.g., neighborhoods) are geographically delineated and the extent to which these areal units deviate from the true geographic context. It is a significant methodological problem because it means that analytical results can differ for different delineations of contextual units even if everything else is the same. Drawing upon Kwan (2012) and recent social science studies (especially environmental health and neighborhood effects research), this article further elaborates on the nature of the UGCoP and explores how recent advances in geographical information system (GIS) and geospatial technologies can help address the problem. It discusses possible means for mitigating the UGCoP, especially with regard to the collection of detailed individual space–time data with global positioning systems, construction of individual activity spaces, and the use of qualitative and web-based GIS to capture people's activity locations and everyday experiences. It also discusses the challenges for future research that seeks to address the UGCoP.