Among the OSM communities throughout United States, that of greater Miami is relatively small and underdeveloped. Miami’s own OSM data availability is comparatively sparse. Nevertheless, the open data effort is growing in Miami, and the county-level government, among others, has made significant improvements in its data discovery and accessibility platforms. A multitude of publicly-available geospatial datasets are ripe for batch upload into Miami’s OSM. Various technical concerns accompany any batch upload, though, and the process can be challenging without a strong collaborative community guiding the workflow. This talk will describe the process undertaken to improve Miami’s OSM by batch uploading a building footprint polygon dataset into the OSM, highlighting some of the challenges and technical issues that users should be aware of.