A rare case that relates benign prostatic hyperplasia-associated bladder diverticula and obstructive uropathy to extrabiliary obstructive jaundice in an older patient is presented. Immediate decompression of the bladder allowed for prompt restoration of the biliary drainage and normalization of the creatinine within a few days. A hepatobiliary etiology was discarded through prompt radiologic and serologic testing along with computed tomography-guided liver biopsy. Long-term management included open suprapubic prostatectomy and diverticulectomy. This unusual case expands the amount of sound anatomic and pathophysiologic links between urinary and extraurinary manifestations.