Abstract: A computer system for intelligently parsing digital content and generating questions based upon the digital content can be configured to receive a digitally encoded file. The system can extract text content from the digitally encoded file. The system can then process the text content through an intelligent text analysis process. The intelligent text analysis process can identify key phrases within the digital content. The system can generate a question based upon a particular key phrase by manipulating a portion of the extracted text content. Further, the system can display, on a display device, the generated question.