An information handling system is disclosed for generating tags of a file including a document or a webpage posting. The generating tags of a file include converting a webpage posting to a PDF document. The method further includes extracting tags provided by users. The method includes scanning the extracted data from a glossary PDF document to identify keywords of the glossary PDF document in accordance with a sentence length. The method further includes extracting data from the PDF document and scanning the extracted data to identify keywords of the PDF document in accordance with a sentence length. The method further includes reapplying selected keywords to the tags of the file.