Deep infiltrating endometriosis of the rectum is a severe disease concerning young women of reproductive age. Because it is a benign condition, aggressive surgical treatment and subsequent complications are not always accepted by young patients. Two surgical approaches exist: the radical approach, employing colorectal resection; and the conservative approach, based on rectal shaving or full-thickness disc excision. At present, the majority of patients with rectal endometriosis worldwide are managed by the radical approach. Conversely, as high as 66% of patients with colorectal endometriosis can be managed by either rectal shaving or full-thickness disc excision. Most arguments that used to support the large use of the radical approach may now be disputed. The presumed higher risk of recurrence related to conservative surgery can be balanced by a supposed higher risk of postoperative bowel dysfunction related to the radical approach. Bowel occult microscopic endometriosis renders debatable the hypothesis that more aggressive surgery can definitively cure endometriosis. Although most surgeons consider that radical surgery is unavoidable in patients with rectal nodules responsible for digestive stenosis, conservative surgery can be successfully performed in a majority of cases. In multifocal bowel endometriosis, multiple conservative procedures may be proposed, provided that the nodules are separated by segments of healthy bowel of longer than 5 cm. Attempting conservation of a maximum length of rectum may reduce the risk of postoperative anterior rectal resection syndrome and subsequent debilitating bowel dysfunction and impaired quality of life. Promotion of less aggressive surgery with an aim to better spare organ function has become a general tendency in both oncologic and benign pathologies; thus the management of deep colorectal endometriosis should logically be concerned, too.