Cholecystectomy is one of the most commonly performed abdominal surgeries in which bile duct injury and bile leaks are the most important complications. Imaging plays an important role in the prompt diagnosis and management of bile leaks. The more common sites of bile leak are the gallbladder bed, subhepatic, in a bilioma, right paracolic gutter, or diffusely in the peritoneal cavity. Bile leak into the lesser sac (LS) is uncommon but is a special entity posing difficult problems in management. We have described in this study the clinical presentation, imaging findings, and management of 6 patients with biliary leakage into the LS postcholecystectomy. The clinical presentation of this condition was varied, ranging from patients with asymptomatic or with vague complaints resulting in difficulties in clinical suspicion or symptomatic but minimal enough not to be detected by ultrasonogram. Hepatobiliary scintigraphy played an important role in the diagnosis and management, and all patients required definitive therapeutic drainage procedures. Any persistent focal radiotracer activity in the anatomy of the LS, increasing with time and not diffusing into the general peritoneal cavity is diagnostic of bile leak into the LS.