OpenStreetMap (OSM) is the most popular, and arguably most successful, volunteered geographic information (VGI) project. The scale of OSM’s goal of mapping the world through individual contributions necessitates a long development time, while the ever-changing nature of the real landscape precludes the possibility of ever “completing” the map. Thus, OSM is a living dataset. With this perspective in mind, we reexamine the motivations for contributing to OSM and the outputs of those motivations. Whereas a pathway from motivation to mapping may explain any individual contributor’s experience, we argue the whole OSM project represents a more complex system in which biased and missing data can be both a driver and a consequence of the VGI model of collaboration. We also reflect on the ways in which the exogenous shock of the proliferation of generative and geoAI may disrupt this system.