Abstract: A cutting bit assembly for attachment to a tool holder of a milling-type machine includes a cutting tip, a cylindrical shank extending from the cutting tip and comprising a rotation-limiting surface, and a spring clip surrounding a body of the shank. The spring clip includes a protrusion configured to interact with the rotation-limiting surface of the shank to limit rotation of the shank relative to the spring clip. The spring clip includes a contracted configuration and an expanded configuration, and in both the contracted configuration and the expanded configuration the protrusion interacts with the rotation-limiting surface.

Abstract: A cutting bit assembly for attachment to a tool holder of a milling-type machine includes a cutting tip, a generally cylindrical shank extending from the cutting tip and comprising a rotation-limiting surface, and a spring clip surrounding a body of the shank. The spring clip includes a protrusion configured to interact with the rotation-limiting surface of the shank to limit rotation of the shank relative to the spring clip. The spring clip includes a contracted configuration and an expanded configuration, and in both the contracted configuration and the expanded configuration the protrusion interacts with the rotation-limiting surface.

Abstract: A cutting bit assembly for attachment to a tool holder of a milling-type machine, including a cutting tip, a generally cylindrical shank extending from the cutting tip, a spring clip surrounding a body of the shank and including a contracted configuration and an expanded configuration, and a washer having an installed configuration in which the washer is disposed on a shoulder of the shank and an uninstalled configuration in which the washer surrounds the spring clip and retains the spring clip in the contracted configuration. At least one of a distal edge of the spring clip or a proximal edge of a bore of the washer comprises a bevel or radius.