Routine placement of transurethral catheters can be challenging in some situations, such as urethral strictures, severe phimosis and false passages. Intravaginal retraction of the urethral meatus can complicate Foley placement in postmenopausal females. In men, blind urethral procedures with mechanical or metal sounds without visual guidance or guidewire assistance are now discouraged due to the increased risk of urethral trauma and false passages. Newer techniques of urethral catheterization including guidewires, directed hydrophilic mechanical dilators, urethral balloon dilation, and direct vision endoscopic catheter systems are discussed, along with the new standardized protocol for difficult transurethral catheter insertions. Suprapubic catheter placement techniques, including percutaneous trocars and the use of the curved Lowsley tractor for initial suprapubic catheter insertion, are reviewed. Prevention and management of common catheter-related problems such as encrustation, leakage, Foley malposition, balloon cuffing and frequent blockages are discussed.