A 79-year-old gentleman presented to the Emergency Department (ED) with catheter-related issues on a background of a long-term catheter for previous urinary retention, Hartmann's procedure for colorectal cancer, and brachytherapy for prostate cancer. A 3-way silicone catheter was placed by ED staff and bladder irrigation commenced. The urine draining following catheterisation was found to be dark and thick, and irrigation fluid was noted to be draining per rectum. CT imaging was performed and demonstrated the catheter tip extending through the posterior wall of the urethra and into the rectum. The patient was admitted under the urology team, and urinary diversion was achieved with a suprapubic catheter. Subsequent imaging demonstrated a periprostatic abscess, which was initially managed with antimicrobial therapy, followed by attempted image-guided drainage. Repeat imaging following a 6-week course of antibiotics failed to show an improvement in the collection. During his inpatient stay, he contracted COVID-19 and passed away suddenly. This case demonstrates the potential catastrophic consequences associated with urethral catheterisation.