Solving complex, ill-structured problems may be effectively supported by case-based reasoning through case libraries that provide just-in-time domain-specific principles in the form of stories. The cases not only articulate previous experiences of practitioners, but also serve as problem-solving narratives from which learners can acquire meaning. The current study investigated the effects of different case-types (success, failures) on analogical transfer to similar problems. In the first week, undergraduate sales management students (N = 36) were assigned to different case library treatments (success, failure) and asked to construct a multifaceted argument (initial argument, counterargument, rebuttal) to resolve an ill-structured, decision-making hiring problem. In the following week, students constructed an argument to solve a novel case without the support of the case library. Data analysis revealed the failure-based case library condition produced significantly higher scores on measurements of counterarguments and holistic argumentation scores on both tasks. A discussion of the implications for pedagogy and instructional design are also presented.