For this study, we reviewed 56 standard-of-care CT examinations over a timespan of 2 years from patients with superior thoracic inlet venous obstruction and identified eight thoracic collateral pathways for venous blood return to the right heart. We evaluated each pathway individually from an anatomic and a pathophysiologic perspective for a better understanding of how such pathways form and what patterns can be expected. All 56 patients were scanned according to our standard CT protocol. Images of the thoracic region were acquired in the craniocaudal direction during breath-holding using a second-generation dual-source CT scanner. Contrast medium was administered via a cubital or antecubital vein; the amount of contrast material ranged from 49 to 81 mL depending on patient body weight. Of the 56 patients, CT showed superior vena cava syndrome exclusively in 22 (39%) patients and showed superior vena cava syndrome and involvement of the left or right brachiocephalic vein or even the subclavian vein in the remaining 34 (61%) patients. We could not find any remarkable feature leading to the formation of only one collateral pathway or to a specific pattern depending on underlying cause or the level or the extent of obstruction. Thus, we believe that there are no specific patterns for how these venous detours form and that they are most probably driven by pressure gradients. Recognizing imaging findings associated with venous collateral pathways may prevent misdiagnosis or unnecessary follow-up examinations. Furthermore, knowledge of these collateral pathways and an understanding of the underlying cause can support interventional radiologists and vascular surgeons in planning interventional procedures and revascularization procedures.