Abstract: A drill bit is disclosed including a rigid cutting tool elongated along a central axis having opposed sides, where one side includes a cutting edge and an opposing side includes a shank for selective engagement with a drill chuck. The drill bit includes a first light path capable of communicating light between the shank side of the drill bit and the cutting edge side of the drill bit. The drill bit may be used with a breach assessment mechanism including a light source configured to provide selective illumination along the light path and a light sensor. Processor logic may be programmed to assess signals from the light sensor indicative of reflected light from a cutting surface contacting the cutting side of the drill bit.