Challenge of Discovery: Recent large-scale initiatives focused the attention of the Smathers Libraries at the University of Florida on the need for significantly expanded and enhanced metadata for our digital collections, both retrospective and prospective. This requires 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. Projects that are described include the new genealogical initiatives with Internet Archive and Family Search, Portal of Florida History, the Digital Library of the Caribbean (dLOC) and the Cuban Heritage Initiatives. We have concluded the pilot project on automated indexing and metadata generation for the Portal of Florida History using 25,000 full text records and the JSTOR thesaurus instead of the Library of Congress subject headings to automatically index the collection and create a search portal. This paper gives a report on the results of the pilot and early application of the process to the entire UF Digital Collections to extract information from our complete digital collections (over 600,000 items/12 million pages) for the Portal. Results of the pilot show significantly increased retrievability, greater depth of accessibility via detailed subject metadata and then explores application to the entire digital collection. The idea of a more automated processes going forward to allow traditional cataloging to focus on the things that need individual attention and use automated tools to develop and improve metadata for other materials is explored since the large number of items (over 12 million and growing at 100,000 pages per month) makes it impractical to use traditional means. We are working with tools that have been developed for information products and services, but can be applied effectively to library collections. This paper covers three of the main themes of the conference: 1) Exposing Grey Literature to Wider Audiences using an open search portal 2) Confronting Obstacles in Accessing Grey Literature through limited metadata tagging and keeping the collection access obscure as sub sets of the Library OPAC, and 3) the Digital Preservation project covering everything from old newspapers, personal papers and county historical collections is the Lifeline for Grey Resources but if not widely available through the internet and deeply tagged using a controlled vocabulary the simple scanning of papers only creates the new microfilm dilemma of locking data away in in accessible places.