In this webinar for ASERL, leaders from the University of Florida’s Smathers Libraries describe several recent, large-scale initiatives that surfaced the need for significantly expanded and enhanced metadata for UF's digital collections, both retrospective and prospective. This required implementing new tools and changing roles and responsibilities for cataloging/metadata staff, including the application of automated processes, improved and consistent metadata practices, and the development of new taxonomies. UF recently concluded a pilot project in partnership with Access Innovations, Inc. to automate the indexing and metadata generation for the Portal of Florida History. Using 29,000 full-text theses and dissertations and the JSTOR thesaurus instead of the Library of Congress subject headings, this process automatically indexes the collection and creates a new search portal. Results of the pilot show significantly increased retrievability, greater depth of accessibility via detailed subject metadata, and explores application to the entire digital collection. Presenters discuss the processes used, impacts on staff, and basic information about business models.