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Gangrenous cholecystitis and perforation are severe complications of acute cholecystitis, which have a challenging preoperative diagnosis. Early identification allows better surgical management. Contrast-enhanced computed tomography (ceCT) is the current diagnostic gold standard. Contrast-enhanced ultrasonography (CEUS) is a promising tool for the diagnosis of gallbladder perforation, but data from the literature concerning efficacy are sparse. The aim of the study was to evaluate CEUS findings in pathologically proven complicated cholecystitis (gangrenous, perforated gallbladder, pericholecystic abscess). A total of 8 patients submitted to preoperative CEUS, and with subsequent proven acute complicated cholecystitis at surgical inspection and pathological analysis, were retrospectively identified. The final diagnosis was gangrenous/phlegmonous cholecystitis (n. 2), phlegmonous/ulcerative changes plus pericholecystic abscess (n. 2), perforated plus pericholecystic abscess (n. 3), or perforated plus pericholecystic biliary collection (n. 1). Conventional US findings revealed irregularly thickened gallbladder walls in all 8 patients, with vaguely defined walls in 7 patients, four of whom also had striated wall thickening. CEUS revealed irregular enhancing gallbladder walls in all patients. A distinct wall defect was seen in six patients, confirmed as gangrenous/phlegmonous cholecystitis at pathology in all six, and in four as perforation at macroscopic surgical inspection. CEUS is a non-invasive easily repeatable technique that can be performed at the bedside, and is able to accurately diagnose complicated/perforated cholecystitis. Despite the limited sample size in the present case series, CEUS appears as a promising tool for the management of patients with the clinical possibility of having an acute complicated cholecystitis.