Congenital Von Willebrand Disease (VWD) is the most common bleeding diathesis in humans with a prevalence of one percent in the general population. However, acquired Von Willebrand Syndrome (aVWS) is a rare coagulopathy that has been reported to be associated with numerous conditions and occurs through a variety of mechanisms. In addition to causing bleeding diathesis due to coagulopathy, there is evidence that demonstrates Von Willebrand’s Factor (VWF) deficiency leads to aberrant blood vessel formation. Treatment for this disease is directed at stabilization of associated hemorrhage and correction of underlying etiology. We present the case of a patient with aVWS disease due to relapse of Chronic Lymphocytic Leukemia (CLL) complicated by gastrointestinal hemorrhage from gastric and small bowel angiodysplasia treated with rituximab and venetoclax, previously unreported in the medical literature.