Instructional designers can support ill-structured problem solving through case libraries that detail domain-specific principles. In this design project, case libraries were employed in an undergraduate sales management course to contextualize knowledge and describe the ill-structured nature of how solutions are derived to solve authentic problems. Whereas many learning environments employ examples of model behavior (Jonassen, 2011), this instructional design was innovative in that the case libraries consisted of sales management failure experiences as the means to facilitate learning. The failure cases embedded within the learning environment engendered design tensions on multiple levels throughout the instructional design. Specifically, this article discusses the issues of engaging the subject matter expert (SME) to talk about failure cases and subsequent challenges to translate the experiences into meaningful learning resources for ill-structured problem solving. Other challenges included how to strategically design the learning environment so that the case library was available at the optimal time for the learners. The design case concludes with a reflection upon the process.