Venous insufficiency is a potentially debilitating condition causing symptoms such as tiredness in the legs, chronic pain, and in many instances ulcerations and skin changes. Although the diagnosis of venous insufficiency by duplex ultrasound has been previously described in the literature, there are cases that present to the vascular laboratory with unusual presentations of venous insufficiency. The case described in this study is one such presentation. The use of duplex ultrasound in this case was instrumental in determining the clinical pathway for the treatment of his chronic venous disease.