The emergence of the free flap in the 1970’s revolutionized head and neck reconstruction changing both reconstructive and treatment paradigms. With time, we have become more comfortable and reliant on these flaps while often abandoning prior techniques and exploration of loco-regional reconstructive options. At this point it’s important to ask ourselves – when does the pendulum swing too far? Cutaneous malignancy is the most common type of cancer in the United States and rising owing to many factors including an aging baby boomer population and higher incidence of immunosuppression. Many of these cases are presenting as higher risk primaries in advanced stages leading to larger Mohs and surgical defects. This population often presents with a special set of considerations including advanced age, numerous comorbidities, cognitive decline, inability to travel, and lack of caregiver support. Benefits to loco-regional reconstruction over free tissue include shorter hospitalization, no need for microvascular expertise, no need for intensive care, decreased cost, and decreased complication rates. In general, we find that in following the reconstructive ladder, perhaps less truly is more in the right setting.