Surgery on patients with malignant obstructive jaundice carries formidable morbidity and mortality rates. Clinical records of 120 consecutive patients who had a serum total bilirubin levels of 100 mumol/L or greater before exploration were analyzed retrospectively to provide guidelines for better management. Although most patients underwent bilienteric bypass to either the extrahepatic (n = 45) or intrahepatic ductal system (n = 28), resection was possible in 32 (26.7%). Complications developed in 42 patients (35%), among whome 12 (10%) required reexploration and 32 (26.7%) died within the same hospitalization. Identification of risk factors associated with hospital deaths after surgery was conducted on 84 of the 120 (group A) patients randomly selected from the entire study period. Based on multivariate analysis, age greater than 65 years, a raised serum aspartate transaminase value greater than 90 IU, and serum urea level greater than 7 mmol/L before surgery were the risk factors selected from 39 different clinical (n = 6), laboratory (n = 26), and operative (n = 7) parameters studied. The predictive value was validated in the remaining 36 patients (group B), and a high-risk patient population had been isolated. Because both serum urea and aspartate transaminase values correlated significantly with the necessity of urgent exploration, aggressive nonoperative treatment should be used to control the emergency. Alternative therapeutic options or perioperative management should be considered for the selected high-risk patients before definitive surgical biliary decompression.