Knowledge transfer has been an important issue for organizational knowledge management programs. This article reviews the plethora of user-generated video activity and the issues it creates for knowledge management activities. Video’s media richness combined with its ability to convey rich narratives can facilitate sensemaking and learning. However, structure and culture are important factors that must be considered in story telling activities to increase the opportunity for effective sensemaking and message retention. Evidence and arguments are presented that should motivate organizations and academics to review video generation activities both internal and external to the organization. Issues concerning video content delivery, liability, spam, and search engine capabilities are discussed. Opportunities for new research inquiries are identified.