The treatment outcome of advanced squamous cell carcinoma involving the head and neck is well known to be dire and usually needs multimodality treatment even including optimal reconstruction after ablative surgery. When a significant area of the soft tissue is resected, reconstruction of oral cavity or pharynx needs to minimize morbidities while achieving adequate functional outcomes. For the better functional outcome, invasive approaching procedures such as lip and jaw splitting, or extensive floor of mouth or pharyngeal muscle ablation should be avoided. Without these surgical procedures, reconstructive surgeons may encounter technical difficulties in flap inset due to deep and narrow space after head and neck cancer resection. In a deep and narrow surgical defect, accurate approximation and suture is extremely difficult. Eventually, repeated flap manipulation and stretch might be inevitable, and even pedicle kinking or injury could happen. Herein, we suggested the “parachute” technique, which was generally used in blood vessels or aortic valve suturing in a narrow surgical field and for avoiding mismatched suture. We applied this “parachute” technique for free-flap inset to head and neck defect, and we herein report our successful outcomes.