This chapter discusses the case of a 67-year-old man, who presented with a short history of uncomfortable flatulence and rectal bleeding. The patient proceeded to abdominoperineal resection with en bloc cystoprostatectomy. The pelvis and perineal defects were reconstructed with a right vertical rectus abdominis myocutaneous (VRAM) flap. Histopathological examination of the resected specimen showed residual microscopic foci of moderately differentiated adenocarcinoma within a 10mm tumor scar. The final pathology showed no rectal tumor involving the prostate but did show evidence of fibrosis consistent with the presence of tumor prior to chemoradiotherapy. Accurate radiological assessment of the extent of tumor after downsizing chemoradiotherapy is extremely difficult. Even when reviewed in hindsight with knowledge of the final pathology, no clear plane could be seen between rectal tumor and prostate. It would certainly have been a risk oncologically to just remove the rectum.