Hooked fingernail deformity can develop after any type of fingertip amputation. A more proximal amputation is associated with a higher probability of developing hooked fingernails. Proximal fingertip amputations with very short remaining nail beds are recommended for revision amputation with nail bed ablation. This procedure eliminates the possibility that the patient may have a functional nail. When the nail matrix is still retained, an oblique triangular neurovascular island flap may preserve the nail and digit length. At our institution, the modified oblique triangular neurovascular island flap is routinely used for patients who underwent fingertip amputation with a retained nail bed. These modifications may aid in preventing the development of hooked nail deformity and creating a round pulp contour without the need for fixation, composite grafts, or distant soft tissue transfer.