Abstract: An insert retention screw comprises a head with a radius that is a sufficient size to fit within a mounting hole of a cutting insert and seat within a seating plane within the mounting hole that is generally perpendicular to the axis of the insert when the screw is at an angle in a range of about 0-15 degrees. The retention screw is provided for holding a cutting insert in the pocket of a tool body. The pocket is partially defined by a floor and a seating surface. A threaded hole is at an angle that is taken with reference to the pocket floor. The insert has a mounting hole passing therethrough. The retention screw passes through the mounting hole and threads into the threaded hole so as to draw the insert against the seating surface.