Gastrointestinal stromal tumors (GISTs) are the most common mesenchymal tumors of the alimentary tract in adults. The most common site is the stomach, followed by the small intestine. The clinical presentation varies from an incidental finding in asymptomatic patients to a large palpable mass causing complications such as bowel obstruction or viscus perforation. The best imaging modality is a CT scan of the abdomen. Treatment is determined by the size and location of the GISTs. Surgical intervention is considered for resectable tumors, while tyrosine kinase inhibitor therapy is considered for irresectable, metastatic, or recurrent GISTs. In this case report, we present a 30-year-old female who is a known case of gastric GIST and liver metastases. She presented to the emergency department with intestinal obstruction secondary to a recurrent GIST abdominal mass and underwent emergency laparotomy for mass resection. Following surgery, the patient developed aspiration pneumonia, which was treated with proper antibiotics. She was discharged in stable clinical condition with a recommendation to start alternative tyrosine kinase therapy. GISTs are difficult to diagnose preoperatively, as most patients are asymptomatic, and they may present with complications, as in our case, a small bowel obstruction. A proper imaging modality will guide the physician toward the diagnosis, but the final diagnosis will be achieved by biopsy. The diagnosis may be challenging, as small bowel obstruction has many causes, although GISTs should be kept in mind as one of the deferential diagnoses.