Acroangiodermatitis (AAD), also known as pseudo-Kaposi's sarcoma, is an uncommon benign angioproliferative condition most commonly seen in the lower extremities. This condition often presents as discolored patches that progress to painful ulcerations. The list of vascular conditions associated with this diagnosis is vast. Acroangiodermatitis presents similarly to more aggressive conditions such as Kaposi's sarcoma, making histopathologic examination helpful in its diagnosis. We present two cases of AAD in the setting of chronic venous insufficiency.