A cutting insert assembly having an insert pocket having a pocket bore, a cutting insert and a fastening member coupling the cutting insert in the insert pocket. The cutting insert having a cutting insert bore, a first surface, a second surface and a peripheral surface extending therebetween. The first and second surfaces meeting the peripheral surface at first and second peripheral edges, respectively, at least a portion of at least one of the first and second peripheral edges forming a cutting edge. The cutting insert bore having at least two portions, the smallest of which, has an oval cross section allowing a for quick replacing or indexing of the cutting insert, without having to completely remove the fastening member from the pocket bore.