Abstract: Pocket protecting retainable cutter bits used on various mining, excavating, and foundation drilling tools and equipment are disclosed. The invention includes a combination of one or more free spinning wear rings axially mounted in recessed portions of the cutter bit shank and a groove and snap ring retainer. The wear rings are tapered on at least one end to assist in installation and designed to compress as the cutter bits are installed into cutter bit pockets. These wear rings are designed to protect the inside surface of the pocket by acting as a barrier between the spinning cutter bit and the stationary inside surface of the pocket. The cutter bit shank is longer than the cutter bit pocket and when installed passes through the pocket and extends past the axial length of the pocket. A flange is included with the cutter bit to protect the outer surface of the pocket.