Awake fiberoptic intubation (AFI) is often preferred in patients with a difficult airway but is related to major and minor complications. Regional anesthesia can be feasible with a preformulated and resilient plan in those scenarios. We present a case report of a 54-year-old male patient of left carcinoma buccal mucosa with chest skin defect due to iatrogenic tumor implantation scheduled for defect repair. Thoracic Segmental Spinal Anaesthesia (TSSA) was planned with AFI as a preformulated strategy. Satisfactory anesthesia was achieved from T2 to T8. The hemodynamic remained stable and the patient remained awake and comfortable throughout the perioperative period. In conclusion, TSSA can be considered an alternative to general anesthesia in patients with difficult airways undergoing chest skin defect repair using a rotational flap, as long as the anesthetist has the required instinctive knowledge and awareness of the possible difficulties associated with intubation or ventilation.