This case report discusses a 44-year-old male who presented with recurrent epigastric pain after starting Ozempic for weight management, which persisted despite switching to Jardiance. His symptoms evolved into diarrhea and fever while vacationing in Mexico, with notable episodes of bloody stools and greasy, floaty stools upon return home. Despite normal laboratory tests and negative stool pathogen results, a CT scan revealed a mass in the gastric antrum. Subsequent endoscopy and fine-needle aspiration confirmed a gastrointestinal stromal tumor (GIST), classified as T3N0. The patient underwent laparoscopic distal gastrectomy with Billroth II gastrojejunostomy. This case underscores the challenge of diagnosing GISTs due to nonspecific gastrointestinal symptoms, emphasizing the necessity for thorough evaluation in persistent cases. The favorable prognosis associated with T3N0 classification highlights the importance of early identification and surgical intervention. Monitoring for recurrence and considering adjuvant therapy are essential in managing such tumors. This case illustrates the value of multidisciplinary care in addressing complex gastrointestinal conditions.