Acute urinary retention is a common problem in the emergency department. Patients can present in significant distress, necessitating the placement of a urinary catheter. Foley catheter placement can be difficult to accomplish depending on the etiology of the retention and the degree of the obstruction. In the case presented here, we used ultrasound guidance, a guidewire, and a Foley catheter to successfully relieve a patient’s urinary retention after multiple failed attempts.