INTRODUCTION: Crohn’s disease is an inflammatory condition that can present with fistulous communications with extraluminal structures. The presence of urachal remnants that do not communicate with the skin account for 50% of urachal malformations and are generally asymptomatic and benign. CASE DESCRIPTION/METHODS: We present a case of an active duty soldier, with no previous medical history, found to have Crohn’s disease presenting as an enterourachocutaneous fistula. The patient presented to primary care with persistent umbilical drainage that did not resolve with antibiotics given. Computed tomography showed a mass on the dome of the bladder with surrounding inflammation but no extravasation of contrast outside of the bladder during cystography. Ileocolonoscopy revealed a narrowed ileocecal valve with biopsies consistent with active Crohn’s disease. Magnetic resonance enterography showed a fistulous communication from the terminal ileum to a urachal cyst which drained to the skin via the umbilicus. After multi-disciplinary discussion with urology and colorectal surgery, patient will undergo planned cyst, fistula, and terminal ileal resection. DISCUSSION: This case represents a rare presentation of Crohn’s disease. The true prevalence of urachal malformations is unclear; a large number remain undiagnosed until noted on imaging when asymptomatic. Enterourachal fistulas are rare, with only 13 cases reported; cutaneous communication has occurred in only 4 of the 13 reported cases. Cutaneous fistulas are more commonly seen in penetrating Crohn’s Disease given proximity of the bowel to the abdominal wall. In our case, the involved segment of bowel created a cutaneous fistula by way of a patent urachal remnant. This case highlights the ability of Crohn’s disease to mimic more benign conditions. A diagnosis of Crohn’s disease should be considered in patients with umbilical drainage that fails to resolve with antibiotics.