Human Communication in Organizations (HCO) is an introductory college course at Ithaca College, typically taken in the freshman year, in which students from a wide variety of majors examine the basic concepts, issues, and uses of organizational communication including communication theory, superior-subordinate and peer relationships, leadership, conflict and negotiation, problem solving and decision making processes, group dynamics, and presentation skills. HCO students experience the complex nature of organizational communication by immersion in a four-week participatory simulation. Wilensky and Stroup (1999) define participatory simulation as a role-playing situation that utilizes emergent activities in order to help learners concretize abstract content into a personally meaningful understanding. In HCO, the participatory simulation is used to provide students with a role-playing situation that will facilitate a learning environment in which students can experiment and discover how complex dynamic communication systems evolve and how to apply organizational communication concepts to shape that evolution. Since student use of instant messaging and social media sites led the instructor to question if the simulation was losing its authenticity, this article discusses a project designed by the authors to improve the simulation by providing more believable and relevant materials, activities, and communication channels. In order to integrate digital communication technologies that would facilitate student use of these tools for teamwork, the authors designed and developed the following solutions: a mock intranet for the fictitious company, OrgCom Associates which included a discussion board, chat tool, and support materials, and a realistic website for the fictitious client, Knowledge College. This project suggests that the millennials are not able to integrate their supposedly inherent technology adeptness into academic work even when they perceive the digital communication technology as authentic and potentially beneficial. (Contains 4 figures.)