The ways in which geographic information are produced have expanded rapidly over recent decades. These advances have provided new opportunities for geographical information science and spatial analysis—allowing the tools and theories to be expanded to new domain areas and providing the impetus for theory and methodological development. In this light, old problems of inference and analysis are rediscovered and need to be reinterpreted, and new ones are made apparent. This article describes a new typology of geographical analysis problems that relates to uncertainties in the relationship between individual‐level data, represented as point features, and the geographic context(s) that they are associated with. We describe how uncertainty in context linkage (uncertain geographic context problem) is also related to, but distinct from, uncertainty in point‐event locations (uncertain point observation problem) and how these issues can impact spatial analysis. A case study analysis of a geosocial dataset demonstrates how alternative conclusions can result from failure to account for these sources of uncertainty. Sources of point observation uncertainties common in many forms of user‐generated and big spatial data are outlined and methods for dealing with them are reviewed and discussed.