We present an illustrative case of postpartum ovarian vein thrombosis and describe its clinical presentation, differential diagnosis, and management. This pathologic process may produce clinical complications or a catastrophic outcome. These adverse events may be avoided if an expeditious diagnosis is made and appropriate treatment is instituted. This mandates a high index of suspicion, the ability to rule out the presence of other processes that may produce similar symptoms in the postpartum patient, and the appropriate triage of specific patients to either medical or surgical management.