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What are the boundaries of a case study, and what should new evaluators do when these boundaries are breached? How does a new evaluator interpret the breakdown of communication, how do new evaluators protect themselves when the evaluation fails? This chapter discusses the journey of an evaluator new to the field of qualitative evaluative inquiry. Integrating the perspective of a senior evaluator, the authors reflect on three key experiences that informed the new evaluator. The authors hope to provide a rare insight into case study practice as emotional issues turn out to be just as complex as the methodology used.