Demands are being placed on educational institutions to provide course content in new and complex forms to address the needs of an ever more mobile student body. This chapter explores the issues of delivering a normally highly interactive graduate level course using these new technologies within the demands of organizational missions and constraints. We will argue that a course covering topics of organizational technology assimilation is the ideal place to begin this process. It will describe the problems and issues that were faced in one typical course. We will also suggest that this is an ideal area to focus future research in organizational adoption of new technologies that address missions and strategies. The “passing of remoteness” is how one commentator described the phenomenon of the rise of the Internet and other distance-shrinking technologies. Ever since the advent of television, educators have wrestled with the viability of using this technology to reach wider audiences. Educational television facilitated the distribution of high-quality program content in a one-directional fashion. Yet for many educators, this approach lacked the interactive give-and-take so important to the educational process. Video-conferencing has been used heavily in industry to reduce the costs of travel within far-flung organizations. This technology made it possible to meet “face-to-face,” even if the faces were a little blurry and movements were jumpy at best. The visual cues so often considered important in determining if messages were being properly communicated were now available. Immediate visual feedback leads to more productive dialog. Educational institutions have always lagged behind industry in adopting these technologies for two critical reasons. First, there is the psychological barrier that faculty must cross adapting new technologies. One could argue that despite the popular view of “radical academia”, the reality is much more conservative. Changes in curriculum or program delivery can be glacial. Second, and perhaps more critically, the investment in the infrastructure to support these technologies was beyond the means of the organization. Yet these same constraints are tipping the balance toward the requirements to adopt these technologies. Resource constraints, particularly in the area of a scarce, high-quality faculty, competition among educational institutions for market share, and the declining technology costs and improvements in transmission quality are combining to drive experiments in this area. In graduate business education, there has always been an emphasis on the interactive approach to education. Universities pride themselves on, and like to print, glossy brochures about the interactive classrooms where the faculty and students conduct highly charged dialogues on topics of immediacy. One popular form of this dialogue is the case study approach. Similar to the kinds of activities one might find in a law school moot-court experience, potential managers must, with often limited and yet at the same time overwhelming data, process situations, explore options and develop recommendations. The instructor may provide a gentle push based upon the direction the class takes but shouldn’t, assuming good case study pedagogy, be dominating a one-sided presentation. Unlike a lecture in nuclear physics, there is no way to predict the exact direction of the class interests - a very dynamic approach is required. How can the video-conferencing technologies address the needs of this very complex form of the educational experience? This chapter will review our experiences and organizational issues surrounding this issue and raise some future research questions that should be addressed to improve the quality and efficiency of this specific form of education.