Regional flaps remain a cornerstone of head and neck reconstruction. Among their many functions, they serve a vital role in salvage surgery and for those in whom medical comorbidities preclude the use of microvascular free flaps. Recent research has also examined their potential benefit in value-based healthcare metrics such as operative time, cost, intensive care unit care, and length of stay as compared to freeflap reconstruction. The submental island flap is one such entity that is well described and validated to provide predictable, oncologically sound coverage for defects of the lower third of the face and oral cavity. Its application has also been documented for repair of defects of the midface, temporal region, oropharynx, and hypopharynx, albeit less frequently. Since its original description, there have been several modifications of this axial-based flap, though none of a vertically oriented long axis. We describe a case of a vertically based submental island flap for maxillary reconstruction that allowed for debulking and recontouring of prior pectoralis flap and correction of submental ptosis.