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With the growing emphasis being placed upon situated learning theory, designs increasingly implement problem-based learning (PBL) in various educational contexts. However, some of the difficulties instructional designers face include interweaving elements such as breadth, depth, and situated knowledge in a contextualized learning task. This design case details how the 3C3R method was systematically employed to design a PBL learning environment that highlights the effects of environmental toxins on human fertility. We also discuss how a case library learning environment (CLLE) was implemented and designed to support the decision-making process. This design case examines the challenges involved, such as misunderstandings between the SMEs and instructional designer as we contextualized complex issues related to human biology. A discussion of how we designed for multiple solution paths is also included. Lastly, we discuss the challenges of interweaving the ill-structured problem with multiple narratives found in a case library.