Rising affluence and awareness among patients in Singapore have led to an increase in demand for specialist procedures such as orthognathic surgery. Underbite deformity, where the lower jaw is disproportionately longer than the upper jaw is possibly the most corrected dentofacial deformity in Singapore today. However, not so a generation ago. Baby boomers, or in the Singapore context, the Merdeka Generation, often did not have the benefit of such services when they were young and many have uncorrected underbite. With advancing age and a lack of proper care in their younger days, total or partial loss of dentition is common. Many seek to replace their missing or decayed teeth with dental implants. In replacing teeth in a patient with an underbite, do we set the teeth in the original cross bite position or do we aim to reconstruct the dentition into an ideal Class I bite?