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Introduction Pancreatic cancer is a leading cause of death in North America and Western Europe with rising rates in the developing world. Endoscopic ultrasound (EUS) with FNA (fine needle aspiration) is a critical component in the evaluation and diagnosis of pancreatic lesions with a high sensitivity and specificity. In this paper, we report patients at our center who eventually developed pancreatic cancer despite an early negative EUS, and identifying factors that may result in a missed diagnosis.Methods The University of Louisville database was queried for patients who had a Whipple procedure for presumed benign disease and had a pre-operative EUS between 2008 and 2018. Patients who had pancreatic adenocarcinoma on final pathology were identified. Demographic, clinical, EUS, operative, and pathologic details were reviewed for each case in efforts to identify factors associated with failure to diagnose a pancreatic malignancy on EUS.Results Five patients who had pancreatic adenocarcinoma on final pathology were reviewed in detail and their cases are presented in the paper. Four of the patients had dilation of the common bile duct, three had chronic pancreatitis. Two of them had previous surgery on the pancreas or bile ducts.Conclusions All of the patients presented in the paper had variables that made their EUS evaluation challenging. A high index of suspicion must be maintained in patients that do not improve after appropriate treatment of their strictures or pancreatic lesions. In the future, new techniques, such as fine needle biopsy and biomarker assays, may improve diagnosis accuracy.