The presence of gas and free air in the extraluminal space of the intestines is known as pneumatosis intestinalis (PI). There are many different causes of this finding, including gastrointestinal, pulmonary, autoimmune, and many more. It is often difficult to differentiate the etiology and clinical importance of the radiographic evidence on pneumatosis intestinalis due to the unclear pathophysiology causing the disease. To complicate things further, the ominous sign of portal venous gas poses the question of whether surgical intervention is needed. We report two cases both with clinical and radiographic evidence of secondary pneumatosis intestinalis with an associated sinister finding of portal venous gas. The cases differ by urgent surgical intervention versus observation before surgery. In this case series, we emphasize the importance of recognizing the radiographic finding and stress the need for further research to standardize a plan of care, including indications for surgery. We encourage more cases like this to be reported to aid in diagnosing and treating this condition early on with the aim of improving the mortality associated with it.