Purpose: Prune-Belly Syndrome (PBS) is a rare congenital disorder characterised by deficient abdominal wall musculature, bilateral cryptorchidism, and urinary tract abnormalities related to dysplasia of the renal pelvis, ureters, and prostatic urethra. There is considerable variability in the severity of renal dysplasia and degree of ureteric and vesical enlargement. The objective of this report is to provide an example of the manifestations of PBS in adulthood and their possible management. Methodology: We present a case of a 60-year-old male with PBS diagnosed in infancy who presented with urosepsis in the setting of an occluded long-term indwelling urinary catheter (IDC) for chronic urinary retention. Informed, written consent was obtained from the patient for their clinico-pathological information to be presented. Results: Physical examination was significant for the pathognomonic “prune-like” appearance of his abdomen. Computed tomography (CT) of his abdomen and pelvis demonstrated moderate bilateral hydroureteronephrosis stable in appearance from imaging 12 months prior and a markedly enlarged bladder albeit collapsed with an IDC in situ. Of interest, the CT also demonstrates distinct deficiency of abdominal wall musculature in keeping with PBS and an associated hernia containing loops of small and large bowel. Due to practical difficulty with urethral catheterization and patient preference, a suprapubic catheter was inserted for ongoing long-term management. Conclusion: Given the rarity of PBS and the marked radiological findings presented, this case is particularly informative in providing an illustrative example of possible genitourinary complications of PBS as well as the challenges in managing concomitant bladder dysfunction.