A 22-year-old healthy man presented to the emergency department with worsening left flank and testicular pain. Lower abdominal pain and lower urinary tract symptoms, were also noted. Contrast-enhanced CT demonstrated several vascular malformations: both common iliac veins converging to an infrarenal inferior vena cava (IVC) with an absent cephalad IVC. Multiple collateral veins were noted, and both the Azygos and Hemiazygos veins were seen dilated, serving as an alternative venous drainage path due to the interrupted IVC. The patient's CT was also notable for several pathologies: bilateral iliac vein thrombosis and left-sided testicular vein thrombus with surrounding fat stranding, suggestive of testicular vein thrombophlebitis. The patient was admitted, and received antibiotic and anticoagulation treatment, with clinical improvement. Hypercoagulability work-up was obtained, and the patient was found to be heterozygous for Factor V Leiden. Interrupted IVC with azygos continuation is an uncommon, and mostly a benign vascular malformation, resulting from abnormal development of IVC-contributing segments during embryogenesis. It is associated with lower limb deep vein thombosis and hypercoagulable states. It is imperative for radiologists to be acquainted with this entity, in order to avoid misdiagnosis. Testicular vein thrombosis is uncommon, mostly associated with prothrombotic disorders, and it should be considered when coagulopathy is suspected.