Background: Early cholecystectomy has been recommended for patients with acute cholecystitis and gallstone pancreatitis. However, patients with pancreaticobiliary malignancy may present acutely with similar symptoms. We hypothesize that the diagnoses of these malignancies may potentially be delayed as an unintended consequence of expedited cholecystectomies. This study reviews a cohort of patients who underwent pancreaticoduodenectomy (PD) to identify those who underwent a separate cholecystectomy before their PD. Methods: We retrospectively reviewed 162 PDs performed between 2012 and 2022. Data collected included: demographics, disease etiology and the presence of cholelithiasis. We identified patients who had a previous cholecystectomy and the time elapsed before PD as well as procedures done during the interval. We reported detailed case summaries on those patients who had a cholecystectomy within 1 year of PD. Results: In the entire cohort, mean age was 65 years, 54% were males, and 83% had a malignant reason for PD. Thirty-one patients had cholelithiasis with 23 (14%) patients having had previous cholecystectomy. Six patients had cholecystectomy within 1 year of PD. They had the following malignancies: ampullary-3, pancreas-1, cholangiocarcinoma-1 and neuroendocrine-1. Four of these patients had expedited cholecystectomy on their index hospital admission and were later found to have a periampullary malignancy with further work up. Conclusions: Pancreaticobiliary malignancies can be difficult to diagnose, and surgeons should not overlook these potential diagnoses when considering expedited cholecystectomy. Future studies in large cohorts are needed to identify high risk candidates who should undergo more detailed testing to exclude malignancy before proceeding with cholecystectomy.