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Patients with Crohn's disease and colonic inflammation that proves refractory to medical therapy often require a proctocolectomy and end ileostomy. Disease recurrence can occur despite creation of an end ileostomy and may lead to peristomal complications such as fistula formation, abscesses, stoma retraction, or strictures. We present the case of a 51-year-old man with medically refractory ileocolonic Crohn's disease who underwent a proctocolectomy with end ileostomy. The disease course was complicated by recurrence of ileal Crohn's disease despite biological therapy. The patient presented with peristomal complications including an enterocutaneous fistula, stoma retraction, and an ileal stricture necessitating surgical revision of the ileostomy. Review of literature confirms an approximately 30% risk of recurrence of Crohn's disease after an end ileostomy. A penetrating phenotype and preexisting ileal disease are risk factors for disease recurrence. A thorough evaluation of the stoma/peristomal area and evaluation of the small bowel by ileoscopy and small bowel imaging are required to assess the extent of disease and extraluminal complications such as stomal retraction and fistulas that require further surgical intervention. While postoperative medical treatment with immunosuppression or biological therapy is often employed, these therapies are unproven to prevent postoperative recurrence in the setting of a stoma.