Acute obstructive suppurative pancreatic ductitis (AOSPD) is a rare form of infection primarily arising within the pancreatic duct in the setting of chronic pancreatitis. We present a case of AOSPD precipitated by obstructive adenocarcinoma of pancreatic head in an elderly woman with a past medical history of chronic pancreatitis, alcohol use disorder and, advanced dementia, who developed progressive abdominal pain during her hospital admission for urinary tract infection. Endoscopic retrograde cholangiopancreatography (ERCP) with balloon sweep of pus and stent placement resulted in prompt abdominal pain resolution. Our case highlights a rare presentation of AOSPD as a harbinger of pancreatic malignancy.