To evaluate the prognostic value of pre-and perioperative factors for voiding dysfunction after surgery for deep infiltrating endometriosis (DIE). Design: Single-center retrospective cohort study. Setting: University hospital. Patients: A total of 198 women with DIE in the posterior compartment who underwent surgery and a postoperative bladder scan. Interventions: Surgical resection of the DIE nodule from the dorsal compartment. Measurements and Main Results: After surgery, 41% of the patients initially experienced voiding dysfunction (defined as >100 mL postvoid residual urine volume at second bladder scan). The number decreased to 11% by the time of hospital discharge. Among those with a need for self-catheterization after discharge (n = 17), voiding dysfunction lasted for a median of 41 days before a return to normal bladder function, with a residual urine volume of <100 mL. The preoperative presence of DIE nodules in the ENZIAN compartment B was associated with postoperative voiding dysfunction (p = .001). The hazard ratio for elevated residual urine volume was highest when the disease stage was B3 (hazard ratio 6.43; CI, 2.3−18.2; p <.001), describing a nodule diameter of >3 cm in lateral distension. Receiver operating characteristic curve analyses showed that a first residual urine volume >220 mL has a good predictive value for the risk of intermittent selfcatheterization (area under the receiver operating characteristic curve 0.893; p <.001). Conclusion:Postoperative voiding dysfunction is frequent; of note, in most cases the problem is temporary. When DIE with an ENZIAN classification B is noted intraoperatively and, most of all, when the diameter of the lesion is >3 cm, a higher risk of postoperative voiding dysfunction is to be expected.