Spontaneous iliac vein rupture is a rare diagnosis with less than 40 cases documented worldwide. There are certain similarities between many of the previously reported cases described in the literature and there are various proposed theories as to why patients develop a spontaneous rupture. A delay in diagnosis is not uncommon and the mainstay of treatment is laparotomy. Here, we report a case of a 51-year-old female with lower extremity swelling for 2days who subsequently developed hemorrhagic shock and had to be taken emergently to surgery, where a rupture of the common and external iliac veins was identified. After multiple blood products, vasopressors, and continuous renal replacement therapy the patient expired on day 3 of hospitalization.