Wunderlich syndrome (WS) is a rare triad of flank pain, flank mass and hypovolemic shock and is classically attributed to angiomyolipomata or neoplasms. Treatment is guided by clinical severity: conservative, selective arterial embolization, or nephrectomy. We report an atypical case of a 69-year old man with a pre-existing 9 cm left renal tumor who developed WS secondary to anticoagulation and simple cyst rupture from his contralateral kidney, complicated by abdominal compartment syndrome with hemodynamic instability despite inotropic support and robust resuscitation. Early recognition and source control via radical nephrectomy were essential in securing a positive outcome.