A cutting tool (10) includes a toolholder (12) and a cutting insert (14) removably securable in the toolholder. The cutting insert (14) includes a lower clamping surface (18) with a V-shaped clamping surface (32, 34) on each side of a central portion (28). The toolholder includes a lower clamping surface (56) with an inverted V-shaped clamping surface (62, 64) on each side of the bottom surface (60) formed by a primary clamping surface (62a, 64a) and a secondary clamping surface (62b, 64b). The secondary clamping surfaces (32b, 34b) of the cutting insert (14) contacts the secondary clamping surfaces (62b, 64b) of the toolholder (12) when the cutting tool (10) is brought into a clamped position due to interference between the toolholder (12) and the cutting insert (14), thereby providing a minimum of four clamping surfaces when in the clamped position.