A double-ended parting cutting insert. The cutting insert includes two cutting portions at opposite ends thereof which are oriented at 90° to each other. The cutting insert includes a pair of rake and support engagement grooves, the rake and support engagement grooves of each one of the pair converging in a direction away from a respective cutting portion. An insert holder includes a clamping portion having a resilient upper clamping jaw having an upper engagement ridge and a lower base jaw having a lower engagement ridge. A gap therebetween forms an insert receiving slot that has a slot opening. The upper and lower engagement ridges converge in a direction away from the slot opening. When the cutting insert is releasably attached to the insert holder, to constitute a fastened position of a cutting tool, the cutting insert is located in the insert receiving slot and resiliently clamped therein.

Holders are described herein providing secure clamping and/or positioning of cutting inserts. Briefly, a holder for a cutting insert comprises a base and a slot for receiving the cutting insert, wherein the slot forms an angle with the base ranging from 10 degrees to 60 degrees.

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.