Bryant's sign is defined as ecchymosis at the base of the penis and scrotum and is usually associated with a retroperitoneal bleed or ruptured aortic aneurysm. We report the case of a retroperitoneal paraduodenal bleed which presented with Bryant's sign. Imaging confirmed a pancreaticoduodenal arcade microaneurysm and associated low-grade coeliac artery stenosis (Sutton-Kadir syndrome). Retroperitoneal bleeding can be life threatening and requires prompt diagnosis and management. However, diagnosis can be challenging due to the clinical variation in presentation. The rarity of presentation in this case caused significant uncertainty necessitating a multidisciplinary approach for diagnostic clarity and safe patient care.