<h3>Study Objective</h3> To raise awareness of how complicated second and subsequent surgeries for deep infiltrating endometriosis are. To emphasize the relevance of good quality preoperative imaging when planning the first surgery for suspected DIE. <h3>Design</h3> Observational cohort study. <h3>Setting</h3> Single institution, Single-center endometriosis unit. <h3>Patients or Participants</h3> Five consecutive patients referred for persistent dyschezia after recent DIE surgery and postoperative hormonal support treatment with Dienogest. <h3>Interventions</h3> DIE imaging study protocol and second surgery by Endometriosis unit Surgical team. <h3>Measurements and Main Results</h3> Patients age ranged from 36 to 41 years. All 5 patients had previous DIE surgery within 12 months of referral/consultation in our unit. All patients presented with persistent dyschezia as their main complaint. Only one patient declared fertility desire. Previous surgical procedures included pelvic adhesiolysis (5), rectal shaving (3), subtotal hysterectomy (1), rectal segmental resection (1), unilateral adnexectomy (1) and unilateral oophorectomy. Imaging studies (Ultrasound Endometriosis systematic mapping protocol and pelvic contrasted MRI) depicted gross rectal nodules (1,5-4,5 cm), all of which had transmural rectal infiltration with variable distance to the anal verge (11-6 cm). All surgical procedures included rectal resection (2 discoid, 3 segmental), with 1 patient requiring a protective ileostomy. Operative time ranged from 150 to 210 minutes. All patients were discharged between 3-5 days. Follow up after surgery (8-20 months) show no late complications and no dyschezia recurrence. <h3>Conclusion</h3> An incomplete surgical excision of DIE rectal nodules can result in persistent dyschezia and prompt the need for further complex surgical procedures. We believe the first surgery for DIE should be preceded by an exhaustive clinical and imaging workup to plan an adequate personalized surgical procedure.