Technologies for dynamic automated content discovery include a computing device that determines a contextual part of a document selected by a user and extracts one or more key terms from the contextual part of the document using an automated key phrase extraction algorithm. The computing device may perform a syntactic algorithm, named entity recognition, or the TextRank algorithm. The computing device may calculate a vagueness score for terms of the document by querying a semantic database and select the key terms based on the corresponding vagueness scores. The computing device performs a content search based on the key terms to generate one or more search results and presents the search results to the user. The computing device may associate each of the search results with the corresponding key term of the contextual part of the document, for example by visually highlighting the key term. Other embodiments are described and claimed.