Although diagnosing jaundice is quite simple, elucidating the underlying cause can be challenging. Of particular importance is early identification of patients whose jaundice is secondary to extrahepatic obstruction, or what is erroneously referred to as surgical jaundice. Unfortunately, the clinical and biochemical presentation of biliary obstruction is often nonspecific and indistinguishable from other hepatocellular disorders. Over the past decade, there have been numerous technological advances that have radically changed the diagnostic approach to jaundice. Modern gastroenterologists currently have a large armamentarium of imaging and diagnostic procedures from which to choose. We present a review of the pathophysiology, differential diagnosis, and diagnostic evaluation of obstructive jaundice. Special emphasis is placed on reviewing laboratory tests and imaging studies. We provide a simple and rational algorithm for judicious use of new technology in the work-up of obstructive jaundice.