In this paper, we discuss GeoWeb technologies, specifically those created via volunteered geographic information (VGI) as a means of analyzing the political contours of mapmaking. Our paper is structured around two case studies of VGI projects that allow for consideration for the political efficacy (and potential drawbacks) of these geospatial technologies. We use de Certeau’s constructs of strategies and tactics as a conceptual framing, which allows for a political reading of geographic data couched in the context of everyday life, as well as opening up inquiry into the politics of making, accessing and interpreting spatial data. We conclude by suggesting provocations for future research on the GeoWeb and VGI at the intersection of geography and information science.