Urinary tract infection is a common medical condition encountered in outpatient clinics and emergency departments. Recurrence of urinary tract infections is common. The recurrence can arise from behavioral, mechanical, and physiological factors. Urachal anomalies are very rare congenital clinical entities. We present the case of a 41-year-old woman who presented to the emergency department with dysuria, frequency, urgency, and incontinence. There was no history of fever or flank pain. Physical examination revealed no abnormalities. Initial laboratory markers were within the normal range. However, urinalysis findings showed numerous white blood cells and positive leukocyte esterase and nitrite. While these findings are suggestive of acute simple cystitis, the patient had a concerning history of recurrent urinary tract infections. The urology team advised performing an abdominal computed tomography scan to rule out any structural abnormalities. The patient underwent a computed tomography scan, which demonstrated the presence of a fluid-filled structure arising from the dome of the bladder and extending superiorly toward the umbilicus, representing a vesicourachal diverticulum. The patient underwent surgical resection after antibiotic therapy. The vesicourachal diverticulum is a very rare type of urinary tract anomalies. The case highlights the importance of considering congenital urachal anomalies in patients with recurrent urinary tract infections. A computed tomography scan can make the diagnosis of such anomalies with high accuracy.