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Fifty years ago Robert Holt (1965) argued that knowledge about Freud's cognitive style would help us better understand his thoughts. He further hoped that his essay would attract additional attention to this problem: How did Freud process information? How did Freud make his discoveries? What enabled the obvious and abundant creativity? We've taken Holt's challenge, focusing on one hitherto unexplored aspect of Freud's cognitive style, brought to our attention in a puzzling comment by Martin Bergmann (2011a: 247): ‘We never find Freud saying “This surprised me very much”’. Therefore, we will focus on one facet of Freud's cognitive style, specifically, the experience of surprise in the context of discovery. We first approach the question narratively, as did Holt, and, with the help of PEPWEB (for the first time we believe), in a cull of the Standard Edition (surprise, surprises, surprised, surprising, surprisingly). Eager to answer Holt's call for the study of Freud's cognitive style, we conclude that Freud was open to surprise in the context of discovery.