This article summarizes findings from a nine-year research program investigating how technological affordances might be used as a part of holistic learning environments to support teachers and learners in disciplined inquiry about persistent social issues. We discuss what our findings suggest about the potential and the limitations of technology-supported learning environments for improving learner engagement, empathy, complex reasoning, and decision-making. Finally, we highlight areas for continued research. (Contains 5 tables and 3 figures.)