The internet is more than a place where the Millennial Generation communicates, plays, and shops. It’s also a medium that raises issues central to nearly every existing field of legal doctrine, whether basic (such as Torts, Property, or Contracts) or advanced (such as Intellectual Property, Criminal Procedure, or Securities Regulation). This creates tremendous opportunities for legal educators interested in using the live internet for experiential education. This Article examines how live websites can be used to create engaging and holistic simulations that tie together doctrine, theory, skills, and values in ways impossible to achieve with the case method. In this Article, the author discusses observations stemming from his experiences teaching law courses using live, online role-playing simulations that cast students in the role of attorneys. The Article concludes that such simulations have significant benefits for law students, and surprisingly, can also benefit scholars who use simulations proactively to deepen the synergies between their teaching and scholarship. However, the resources required for simulations may also exacerbate long-standing systemic tensions in legal education, particularly regarding institutional resources as well as the sometimes conflicting roles of faculty as teacher-scholars. Because the American Bar Association will almost certainly, and appropriately, require law schools to expand their simulation offerings, the benefits and tradeoffs of simulations teaching must be addressed now.