Chronic and recurrent abdominal pains are common complaints in children and adolescents, but the evaluation in the emergency department (ED) can be challenging. We present a rare yet serious case of a 17-year-old white female who presented to the ED with a 2-day history of diffuse abdominal pain, nausea, and intractable vomiting. Abdominal examination and imaging, including computed tomography (CT), were negative during an episode 6 weeks previously. This was her fifth similar episode in a 2-month period, and she had been seen at three different hospitals and admitted on each occasion. Three days prior to presentation to our ED, she was seen at a gastroenterology clinic and diagnosed with irritable bowel syndrome and an ovarian cyst. Symptomatic therapy during the current presentation, with intravenous fluids, antiemetics, and parenteral narcotics, failed to alleviate her abdominal pain and vomiting. Emergent CT evaluation revealed a high-grade colonic obstruction with focal circumferential narrowing in the transverse colon and a lower gastrointestinal follow-through radiograph with Gastrografin enema showed a classic “apple-core” lesion. Colonic adenocarcinoma with positive regional lymph nodes was found during emergent exploratory laparotomy. Pediatric patients with recurrent, episodic abdominal pain should undergo systematic evaluation and symptomatic treatment. A previous negative workup should not dissuade emergency physicians from proceeding with a systematic and thorough evaluation of the pediatric patient presenting with abdominal pain and vomiting.