Presentation at the Sixth Annual ECAR/HP Summer Symposium for Higher Education IT Executives, June 11-13, 2007, Boulder, Colorado. In January 2007, Michael Wesch released a video on the history of the Web called "The Machine is Us/ing Us." The video quickly tracks the transformations of the Web from its beginnings as a place to retrieve information into a vibrant user-generated and user-organized platform of RSS feeds, blogs, wikis, social networks, and folksonomies that encourage, enhance, and capitalize on collaboration. At the video's end, Wesch suggests that these transformations require us to begin rethinking virtually everything, from authorship and copyright to our sense of identity and selfhood. These new technologies also have profound implications for education. What possibilities and challenges do they bring to our teaching? What should we be teaching to students who are habituated to a new media environment where Google and Wikipedia are always at their fingertips? How are these technologies changing the way students learn and assess information? In short, we need to rethink how we teach, what we teach, and whom we think we are teaching. For this presentation, Wesch creates another video in the same genre as "The Machine is Us/ing Us." Like the earlier video, this video quickly tracks the important moments in the history of education and attempts to capture the possibilities and challenges of the current moment in such a way as to pose and clarify some of the most important questions facing us as educators today.