An automated drill bit sharpening and verification system employing one or more electronic optical assemblies for gathering orientation data of a drill bit to be sharpened. The drill bit is rotated and aligned to a grinding assembly based on the orientation data. The orientation data of the drill bit may be gathered by illuminating a cutting tip of the drill bit with an illumination ring. Additionally, the orientation data of the drill bit may be gathered by capturing two views (e.g., orthogonal views or front and side views) of the cutting tip of the drill bit.