Postoperative urinary retention (POUR) is a known complication following a variety of procedures, with a reported incidence of 2.1-3.8% in general surgery and up to 52% in anorectal surgery. We report a case of POUR in a female resulting in severe unilateral hydronephrosis with a perinephric urinoma due to a ruptured fornix. The extent of hydroureter caused an axial rotation upon itself producing further outflow obstruction. This phenomenon of an anatomical ureter deformity secondary to urinary retention resulting in a ruptured fornix is an unusual occurrence. The patient underwent a percutaneous nephrogram where a stiff guidewire was successfully passed into the bladder by interventional radiology (IR) and allowed for placement of an indwelling ureteral stent. The case presentation, diagnostic evaluation, and therapeutic intervention are discussed.