The Internet has brought many changes to the way geographic information is created and shared. One aspect that has not changed is metadata. Static spatial data quality descriptions were standardized in the mid-1990s and cannot accommodate the current climate of data creation where nonexperts are using mobile phones and other location-based devices on a continuous basis to contribute data to Internet mapping platforms. The usability of standard geospatial metadata is being questioned by academics and neogeographers alike. This chapter analyzes current discussions of metadata to demonstrate how the media shift that is occurring has affected requirements for metadata. Two case studies of metadata use are presented—online sharing of environmental information through a regional spatial data infrastructure in the early 2000s, and new types of metadata that are being used today in OpenStreetMap, a map of the world created entirely by volunteers. Changes in metadata requirements are examined for usability, the ease with which metadata supports coproduction of data by communities of users, how metadata enhances findability, and how the relationship between metadata and data has changed. We argue that traditional metadata associated with spatial data infrastructures is inadequate and suggest several research avenues to make this type of metadata more interactive and effective in the GeoWeb.