Researchers and teacher educators have called for contextualizing the learning of pedagogy and content within the complex context of schools. This account provides an overview of a web-based simulation called Sim-School[C] that provides a realistic framework for students to contextualize curricular decisions, differentiate instruction and reflect on their practice. The Sim-School[C] project addresses the question: What new opportunities can technology provide to help education programs better prepare preservice teachers for the diversity of school settings and the array of challenges they will face in the future? Qualitative and quantitative results are discussed in the investigation of the project's effectiveness. (Contains 1 note.)