This chapter discusses the case of a 25-year-old man, who was referred to the proctology clinic with rectal bleeding, mucus discharge, and sensation of prolapse. At examination under anesthesia (EUA), advanced circumferential hemorrhoidal prolapse was evident. Stapled anopexy/hemorrhoidectomy (PPH) could be considered, although this can be technically demanding with gross disease. In addition, there are reports of penile trauma from the staple line in homosexuals practicing anal intercourse. Anorectal physiology and endoanal ultrasound examinations were undertaken. These demonstrated low resting pressure but normal squeeze pressure, and intact sphincters. The patient went on to have a repeat Doppler-guided hemorrhoidal artery ligation (DG-HAL) and rectoanal repair (RAR), with a good outcome. Whilst EUA can be useful for planning, it should have been realized that this case was not straightforward, and that Milligan-Morgan hemorrhoidectomy was not ideal. Hemorrhoid treatments in HIV-positive patients should probably be undertaken in centers frequently dealing with such patients.