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Two recent cases, Pillay v. Millard Refrigerated Services, Inc. and Gatto v. United Airlines, Inc., et al., show that some kinds of preservation failures are being repeated despite multiple decisions over the course of many years sanctioning the same types of spoliation. Specifically, Pillay involved a failure to suspend automatic processes that periodically purge data and Gatto involved a failure to preserve social media content. More puzzling still is that these two cases are merely select examples drawn from the most recent case law; they are representative of a much more widespread failure to learn from history.