Crohn's disease is a chronic transmural inflammatory process that primarily affects the gastrointestinal tract, with several extra-intestinal manifestations. Though patients usually present with vague abdominal pain, initial presentation can be at an advanced stage or with extra-intestinal pathology. The authors report the case of a 59-year-old woman, who presented with a tubo-ovarian abscess that resulted in a protracted non-healing enterocutaneous fistula, which was eventually diagnosed as Crohn's disease approximately 2 years after initial presentation. Relevant literature is reviewed, as well as time-points where an earlier diagnosis could have been made thereby underscoring the importance of considering Crohn's Disease in a non-healing enterocutaneous fistula in an otherwise asymptomatic patient.