This paper outlines and discusses the pedagogical approach, the technical design architecture, and an innovative implementation of a collaborative role-play simulation technology (called the Role-Play Simulation Generator). It also includes summative evaluation data derived from a case study application of this technology. The pedagogical approach of this collaborative learning technology is based on the principles of goal-based learning, and learning by doing in authentic environments where students are allowed the opportunity to acquire the intended learning outcomes by making mistakes in safe environments. The technology used to support this environment is Web-based simulation, which has been custom-designed for generating similar learning environments. This work is the continuing effort of a multidisciplinary team comprising subject matter experts, learning design architects and Web-based tools developers at the University of Melbourne and Digital Learning Systems P/L in Australia...