The incarnation of many Internet-based courses is informed by traditional notions of classroom instruction, in which course/content management systems (CMSs) like WebCT and Blackboard are used to reproduce actions undertaken in brick-and-mortar classrooms. In this dissertation I argue that the way in which the CMS is configured and deployed can provide students with the sense that they are immersed in a social activity other than taking a college course. Elaborating on simulation-building methodologies, I show how we have created a CMS called MyCase that helps classroom instructors evoke and immerse students in discourse-demanding situations within several disciplines. This sense of immersion is especially important for communication-intensive courses in which students seek to practice disciplinary and workplace genres whose social motive may not be readily reproducible within the confines of the (computer) classroom;The dissertation details qualitative studies conducted in a management course and a professional communication course of students and instructors who used simulations built with MyCase. Results indicate that students participating in these simulations (1) attribute greater significance for their professional lives to the activities in which they engage within the simulation than they do to other classroom activities and (2) engage in activities that more closely match established definitions of active learning than other classroom activities, including those involving traditional (Harvard) case studies. In addition, by providing concrete examples of student actions, I argue that the affordances of an online environment for simulating time and space enable students to reflect on their practices and even engage in critique and critical practices (ranging from quotidian resistance to organized activism).