Spontaneous rupture of metastatic adrenal tumor with massive retroperitoneal hemorrhage and shock is an uncommon clinical event. Herein, we report a case of hepatocellular carcinoma (HCC), where left hepatic lobectomy and right adrenalectomy for metastatic HCC were performed in April and August 2002, respectively. Subsequently, the patient presented to the emergency room with acute-onset severe left flank and back pain in March 2004, accompanied by a falling hemoglobin level. Computed tomography revealed a 7-cm left adrenal tumor mass with retroperitoneal hemorrhage. The ruptured adrenal tumor was further confirmed by selective angiography, which demonstrated that the bleeder was supplied by the left suprarenal artery. Transarterial embolization (TAE) to stop tumor bleeding was performed successfully. The patient then underwent tumor resection with left adrenalectomy 5 days after the embolization, with pathology subsequently revealing metastatic HCC. The recurrent intrahepatic HCC was controlled with TAE, and the patient underwent hormone replacement therapy with prednisolone 10 mg/day. Metastatic adrenal tumor bleeding should be suspected in hepatoma patients who suffer abrupt flank pain and shock. Hemodynamically unstable patients require supportive transfusions and urgent surgical exploration. Angiographic embolization, if deemed feasible, may be a valuable adjunct for achievement of hemostasis prior to definite surgery.