Objectives Scarring from prior bypass surgery and irradiation may compromise revascularization options in critical ischemia due to underlying occlusive disease. Occlusive disease of the axillo-brachial artery is particularly difficult to revascularize under such hostile conditions. Method We present a case of a 58-year-old woman presenting with a painful, pulseless, and cool left upper extremity. The patient had a known history of left upper extremity occlusive disease which was managed by subclavian–axillary artery stenting with re-occlusion and subsequent extra-anatomic left carotid-to-proximal brachial artery prosthetic bypass, which was complicated by stroke. The patient had a history of left mastectomy, axillary node dissection, and external beam radiation therapy. When considering revascularization options, the combination of post-radiation changes and scarring of the conventional operative zones for revascularization posed a high risk for complications. We describe a novel approach for such revascularization, where the inflow source was the terminal brachiocephalic artery, outflow to the upper left brachial artery, with anatomic intrathoracic-to-axillary tunneling through the thoracic outlet after verifying the lack of dynamic extrinsic compression at that level. Result The procedure resulted in resolution of the symptoms and the patient continued to do well 2 years later. Conclusion This case shows that anatomic tunneling through the thoracic outlet can be a viable option for upper extremity revascularization when hostile conditions preclude other anatomic tunneling routes or extra-anatomic options.