Gastrointestinal stromal tumors (GISTs) are mesenchymal tumors that most commonly have activating mutations in KIT. Recurrence after complete resection remains a significant problem, and the ability to identify patients at high risk for recurrence would allow for selective use of adjuvant therapies such as imatinib in patients who may garner the most benefit. Initial staging systems stratified recurrence risk by tumor size and mitotic index, whereas subsequent staging systems also included tumor location. However, other clinical factors may influence prognosis and the risk for tumor recurrence after surgery. The purpose of this article is to highlight tumor rupture as an additional risk factor that should be considered when assessing for recurrence risk. Tumor rupture is associated with decreased survival and increased recurrence rates, but it is not universally included in current staging systems. Patients with ruptured GISTs may not meet the risk criteria elaborated in some current staging systems, yet these patients are at high risk for tumor recurrence and may benefit from adjuvant imatinib therapy. A fundamental understanding of all the risk factors for tumor recurrence, including tumor rupture, and appropriate consideration for adjuvant therapy through a multidisciplinary approach are requisite for the maximal prevention of disease recurrence.