This document discusses three studies examining how students interact with and solve ill-structured problems presented with either a hierarchical or heterarchical web-based structure. The first exploratory study found that the heterarchical structure led to more collaboration and positive perceptions of organization. The second case study found problem solutions in response to the heterarchical structure were more comprehensive and viable. The third experimental study similarly found that exploration of the heterarchical structure was more comprehensive and problem solutions became more expert-like. However, hierarchical structure initial led to higher quality initial solutions. Overall, the heterarchical structure better supported expert-like problem solving but clearer structure from hierarchical also had benefits initially. More research is needed on user experience design of ill-