Deep invasive gastrointestinal endometriosis (DIGIE) is a frequent and severe presentation of endometriosis. Although most cases invade the rectosigmoid colon, DIGIE can involve any portion of the gastrointestinal tract from the stomach to the rectum, and is commonly multifocal and multicentric. Although histopathologic confirmation with surgery remains the gold standard for diagnosis, ultrasound (US) and magnetic resonance imaging (MRI) are the key non-invasive imaging modalities for initial assessment. US may be preferred as a screening study because of its easy availability and low-cost. Pelvic MRI and magnetic resonance enterography (MRE) provide substantial advantages for disease mapping in the pre-operative period, particularly in extensive bowel endometriosis. Although medical management of DIGIE with hormonal therapy can help control symptoms, disease course can be relentless and require surgical intervention. Surgical options depend on, the location; length; depth; circumference; multicentric or multifocal disease. With procedures including simple excision, fulguration of superficial lesions, shaving, disc excision, and segmental resection. A successful treatment outcome is largely dependent on good communication between the treating surgeon and the radiologist, who can provide vital information for effective surgical planning by reporting the key elements that we elaborate upon in this paper.