Foramen of Winslow hernias are one of the most uncommon types of internal hernias that a surgeon will encounter. They are often initially indolent with vague symptoms that present over an extended period of time. Unfortunately, these hernias are not often diagnosed prior to requiring emergent operative intervention. This case report describes a patient who had a long history of vague abdominal pain and radiographic evidence of a foramen of Winslow hernia 4 years prior to presenting with acute obstructive symptoms. This raises the question: Should foramen of Winslow hernias, if diagnosed early, be repaired on an elective basis?