This chapter describes a new automatic digital content generation system we have developed. Recently, some universities, including Hosei University, have been offering students opportunities to take distance interactive classes over the Internet from overseas. When such distance lectures are delivered in English to Japanese students, there is a pressing need to provide materials for review after class, such as video content on a CD-ROM or on a Web site. To meet this need, the authors have developed a new automatic content generation system, which enables the complete archiving of lectures including video/audio content, synchronized presentation materials, and handwritten traces on virtual whiteboards. The content is generated in real time and is immediately available at the end of the class. In addition, this system incorporates a unique video search algorithm which adopts a phonetic-based search technology. This enables quick review of the video content by typed-in keywords. The system can automatically create a vast amount of digital content and provide students with an efficient learning tool.