Two-thirds to three-quarters of Crohn's disease patients require intestinal surgery for medically refractory disease or complications. Surgery is not a cure and most patients develop recurrent Crohn's disease and require additional intestinal resections. There are a number of medications that have been investigated for preventing and treating recurrence. Risk factors for postoperative disease recurrence help guide the physician in determining the appropriate treatment strategy after Crohn's disease surgery. The approach to Crohn's disease treatment has evolved over the years. No longer should surgery be considered a failure of treatment, rather an important intervention to correct irreversible disease. In combination with a better understanding of postoperative medication strategies, patients with Crohn's disease may achieve longer term remission than previously realized. This review elucidates current understanding of the natural course of postoperative Crohn's disease, monitoring for recurrence, the risk factors for recurrence, and provides insight into an evolving new paradigm for postoperative Crohn's disease treatment.