Obstructive uterovaginal anomalies may present after puberty with amenorrhea, dysmenorrhea, pelvic pain, recurrent vaginal discharge, or infertility. The evaluation of a patient with a suspected obstructive reproductive anomaly should include a detailed medical history, physical examination, and imaging. The genital examination is critical to differentiate a patient with an imperforate hymen from a patient with labial adhesions, urogenital sinus, transverse vaginal septum, or distal vaginal atresia. Pelvic ultrasonography is the initial imaging method recommended for a patient with cyclic pain and amenorrhea or a patient with persistent dysmenorrhea. It is important to note that diagnosis of a uterine or vaginal anomaly by imaging before puberty can be challenging and misleading because of the small size of the prepubertal uterus and the lack of endometrial stimulation and menstrual distention of the vagina. Consultation with a radiologist experienced with imaging of uterovaginal anomalies may be helpful to determine the most accurate diagnosis. In general, obstructive vaginal and uterine anomalies are not surgical emergencies, and the complexities of these conditions are best managed by gynecologic care providers familiar with the surgical management of these conditions. Given the high risk of stenosis and complications associated with transverse vaginal septum, distal vaginal atresia, and cervical atresia, referral to a center with expertise in the management of these anomalies is paramount. The best long-term outcome is achieved with a complete evaluation, clear understanding of the anomaly, mobilization of appropriate surgical resources, sufficient preoperative counseling, and planned surgical intervention.