Urethral diverticulum (UD) in women is rare and can present with non-specific symptoms. The classical triad of dysuria, dribbling, and dyspareunia is present in around 20%. Diverticula are thought to arise as a result of a ruptured blocked paraurethral gland into the urethral lumen. Clinical examination may reveal a lump over the urethra that expresses urine or pus into the urethra on palpation. T2-weighted MRI scanning is the imaging modality of choice, although video urodynamics may also reveal this pathology. Malignancy is rare but can be aggressive, and therefore any conservatively managed UD should be offered surveillance. Transvaginal excision is the gold standard surgical treatment. The commonest cause of urogenital fistula (UGF) worldwide is obstructed second stage of labor-obstetric UGF. UGF are rare in well-resourced countries. They are most commonly related to gynecological or pelvic surgery. A high index of suspicion is the most important diagnostic tool, and careful vaginal examination is imperative. Imaging with CT Urogram (CTU), MRI, and fluoroscopy aids diagnosis and assists operative planning. Medico-legal litigation is often related to a delay in diagnosis or treatment. While spontaneous healing can occur with adequate urinary drainage, this is rare and surgical intervention is often required. Vaginal, endoscopic, and abdominal (open, laparoscopic or robotic) approaches may be employed, depending on the anatomy of the injury and surrounding structures. Urethral stricture in women results in a narrowing of the urethral lumen. It causes voiding and sometimes storage symptoms, pain and urinary infections. It should be carefully differentiated from other structural and functional causes of bladder outflow obstruction. Diagnosis is usually made using uroflow or urodynamics, direct visualization with urethroscopy, or imaging with fluoroscopy. Treatment ranges from conservative management, topical treatments, self-dilation, formal dilation, urethrotomy to urethroplasty.