Theorists have argued instructional strategies that emphasize ill-structured problem solving are an effective means to support higher order learning skills such as argumentation. However, argumentation is often difficult because novices lack the expertise or experience needed to solve contextualized problems. One way to supplement this lack of experience is through case-library learning environments that provide detailed stories of expert problem solving. In the current study, participants were provided three different variations of case libraries when solving an argumentation task: case library with no prompts, case library with retain prompt (focused on understanding an individual case), and case library with retrieval/reuse prompt (focused on understanding similarities with others cases in the case library). This study found that the no prompt and case library with retain prompts outperformed the case library with retrieval/reuse prompts. The finding was found on measurements of counterclaim and overall holistic scores on the transfer task. The findings suggest the design of the cases within the library impacts how the participants adopted the case as a vicarious experience and transferred the experience to solve problems.