Routine urinary catheter placement may cause trauma and poses a risk of infection. Male catheterization, in particular, can be difficult, especially in patients with enlarged prostate glands or other potentially obstructive conditions in the lower urinary tract. Solutions to problematic urinary catheterization are not well known and when difficult catheterization occurs, the risk of failed catheterization and concomitant complications increase. Repeated and unsuccessful attempts at urinary catheterization induce stress and pain for the patient, injury to the urethra, potential urethral stricture requiring surgical reconstruction, and problematic subsequent catheterization. Improper insertion of catheters also can significantly increase healthcare costs due to added days of hospitalization, increased interventions, and increased complexity of follow-up evaluations. Improved techniques for catheter placement are essential for all healthcare personnel involved in the management of the patient with acute urinary retention, including attending emergency physicians who often are the first physicians to encounter such patients. Best practice methods for blind catheter placement are summarized in this review. In addition, for progressive clinical practice, an algorithm for the management of difficult urinary catheterizations that incorporates technology enabling direct visualization of the urethra during catheter insertion is presented. This algorithm will aid healthcare personnel in decision making and has the potential to improve quality of care of patients.