An anti-skive drill bit including a body having a proximal end, a distal end, a longitudinal axis extending between the proximal and distal ends, and a flute extending longitudinally along the body. The distal end includes a distally facing region and a first channel defining a first channel surface. The distally facing region includes a relief surface having a first most-distal point at one of an intersection of an outer diameter of the body and a leading edge of the first flute, and an intersection of the outer diameter of the body and the first channel surface. The distally facing region has a relief surface angle between the relief surface and an outer diameter surface of the body at the first most-distal point of less than 90 degrees. The channel has a proximal end intersecting the first flute, and a distal end intersecting the relief surface.