Abstract: Drilling tools and/or drill bits having notches with buttressed regions and/or notches therewithin to improve notch strength. In some embodiments, the drill/drill bit may comprise a shank comprising a cutting face, the cutting face terminating in a cutting edge. A notch may be formed along the cutting edge, which may be configured to separate chips formed by the drilling tool during operation. A buttressed region may be formed within the notch and may terminate along the cutting edge. The buttressed region may expand a size of the notch in one or more dimensions.