Crohn's disease (CD) has a wide variety of clinical presentations, ranging from abdominal pain to stricture and fistula. Fistulas involving the genitourinary tract can be severe and often require surgical intervention. Given the array of presenting symptoms, a delay in diagnosis can occur. We present the case of a healthy active duty soldier, with no previous medical history, found to have CD through an initial presentation of isolated umbilical drainage. Imaging workup identified an entero-uracho-cutaneous fistula with involvement of the transverse colon. Urachal anomalies are uncommon, and entero-urachal fistula as an initial presentation of CD is exceedingly rare. This case highlights the need to consider CD in the differential for patients with umbilical drainage despite a lack of concurrent more frequent presenting symptoms (abdominal pain, bloody diarrhea, and perianal fistula). Maintaining awareness of uncommon initial presentations of CD can minimize delay in diagnosis and thereby mitigate the risk of severe complications.