Stapled hemorrhoidopexy or Procedure for Prolapse and Hemorrhoids (PPH) has become an accepted alternative to excisional hemorrhoidectomy for treating prolapsing hemorrhoids. Although rare, severe complications have been reported after this procedure. We report a series of four male patients with the unusual but debilitating symptoms of obstructed defecation (OD) after PPH. Presenting symptoms included evacuation difficulty, rectal pain, and urgency. All had scarring and stenosis at their PPH anastomotic staple line with a resultant ball-valve effect in three patients as the mobile, excessive, proximal rectal mucosa prolapsed past this relatively immobile area. The fourth patient had an anterior rectal mucosal pouch distal to the PPH staple line. In three of the four patients the anastomosis was below the dentate line or on an oblique angle. Corrective operative intervention largely relieved OD symptoms. One patient, more refractory to successful revision, was eventually diagnosed and treated successfully for pudendal neuropathy. Avoidance of the complication of OD is possible through careful patient selection, proper operative technique, and consideration of nonsurgical etiologies. These complications are complex in nature but most patients will respond to an individualized treatment plan that combines surgical and medical interventions.