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Chronic pancreatitis (CP) is a known risk factor for pancreatic cancer. CP may present with an inflammatory mass, and differentiation from pancreatic cancer is often difficult. Clinical suspicion of malignancy dictates a need for further evaluation for underlying pancreatic cancer. Imaging modalities remain the mainstay of evaluation for a mass in background CP; however, they have their shortcomings. Endoscopic ultrasound (EUS) has become the go-to investigation. Adjunct modalities such as contrast-harmonic EUS and EUS elastography, as well as EUS-guided sampling using newer-generation needles are useful in differentiating inflammatory from malignant masses in the pancreas. Paraduodenal pancreatitis and autoimmune pancreatitis often masquerade as pancreatic cancer. In this narrative review, we discuss the various modalities used to differentiate inflammatory from malignant masses of the pancreas.