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Gall bladder perforation is a rare but serious complication of acute cholecystitis. Gall bladder perforations commonly occur in patients with comorbidities and in association with gall stones. We report a rare occurrence of intrahepatic type II perforation of the gall bladder in a previously healthy elderly male with acalculous cholecystitis. Lack of early positive findings related to clinical assessment, laboratory workup, and imaging resulted in a challenging diagnosis. High degree of clinical suspicion and close monitoring in such patients is necessary to detect early deterioration and improve outcomes.