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Leiomyosarcomas of the inferior vena cava (IVC) are uncommon malignancies. There is limited research detailing optimal diagnostic and clinical management. Here, we present 2 unique cases of IVC leiomyosarcoma including one in which the mass was partially ruptured through the vessel at initial presentation. We detail radiologic findings, 2 different transvenous approaches for biopsy of these masses, and subsequent oncological management.