Reconstruction of external ear defects often poses various challenges due to the complex anatomy of the ear and its significant role in overall facial aesthetics. The location of the defect independently impacts the repair as various locations present distinct, additional factors to consider during planning. Specifically, defects of the superior auricle complicate the reconstructive process, due to the role of the helical root and superior rim in providing mechanical support for facial accessories such as glasses or hearing aids. The approach to reconstruction must be systematic while also being individually tailored in order to appropriately restore both optimal cosmesis and function. The featured case involves the reconstruction of a full-thickness superior helix and auricular defect in a patient who wears eyeglasses with a cochlear implant on the same side. The discussion highlights the complexity of superior auricular reconstruction as well as the various surgical options used and challenges encountered.