This article advances a continuing line of research that investigates the potential of hypermedia resources and scaffolding for supporting problem-based social studies and developing critical reasoning. Our line of inquiry consists of a series of generative design experiments that informs problem-based curriculum development. Our findings suggest that expert guidance may be embedded into the learning environment to give students conceptual and strategic road maps that assist them in understanding the process of disciplined inquiry. However, our results also emphasize the difficulties in managing the cognitive challenges posed by ill-structured social problems and suggest limits to the embedded support that can be provided for complex thinking. Complex conceptual tasks may require spontaneous support that can only be provided by a skilled teacher. We suggest that embedded scaffolds may be used to support teachers by reducing the amount of spontaneous scaffolding they must do in an ill-structured environment and discuss other steps that might be taken to encourage problem-based inquiry.