Adult intussusception in the setting of inflammatory bowel disease (IBD) is a rare phenomenon. Giant pseudopolyps, while generally considered benign, may function as lead points for intussusception. Diagnosis and management of intussusception in the setting of IBD can be fraught with hazards. We report the case of a 27-year-old male, recently diagnosed with ulcerative colitis and giant pseudopolyps, who presented with colocolonic intussusception and obstruction. Diagnosis was confirmed using CT imaging and the patient underwent resection of the colocolonic intussusception without reduction. The following case underscores the challenges in managing adult intussusception in the setting of IBD and allows for a review of the literature to date. Resection of non-reduced intussusception, rather than endoscopic or enema reduction, should continue to be definitive treatment of patients presenting with this unusual problem.