A rotary cutting tool includes a cutter body having a plurality of insert-receiving pockets. Each pocket includes a bottom support surface, an axial support surface, a radial support surface, a top clearance surface and an intermediate clearance surface extending between the axial support surface and the top clearance surface. A cutting insert includes a helical top surface, a helical side surface, a side surface opposite the helical side surface, a pair of opposed side walls, a bottom surface, and a cutting edge formed at an intersection between the helical top surface and the helical side surface. The cutting insert further includes an undercut for accommodating the axial support surface, the top clearance surface and the intermediate clearance surface of the pocket when the cutting insert is mounted in the pocket.