A prismatic and cylindrical cutting insert for long edge rotary milling applications has multiple indexable cutting edges ranging from four to six or even more depending on the actual milling applications. Each cutting edge of a prismatic or cylindrical cutting insert provides a positive cutting geometry and is equivalent to an indexable cutting edge of a traditional single-sided parallelogram-shaped cutting insert having two indexable cutting edges (often referred as A-Style insert). The prismatic and cylindrical (including tapered or conical) cutting insert may be used for machining a wide range of materials including difficult-to-machine materials, cast-iron and alloys, aluminum and alloys, carbon steels, and fiber reinforced composites.

A cutting insert includes a main surface formed in a substantially parallelogram shape and having a pair of acute angle corner portions and a pair of obtuse angle corner portions, a seating surface that faces a side opposite to the main surface, a side surface that connects the main surface and the seating surface to each other, a corner cutting edge disposed in the acute angle corner portion, and a main cutting edge and a subsidiary cutting edge which are respectively disposed in a pair of side ridge portions of the main surface located each other across the acute angle corner portion. A mounting hole into which the fixing member is inserted penetrates the main surface and the seating surface. The main cutting edge is inclined at an inclination angle equal to or larger than 8° with reference to a plane perpendicular to an axial direction of the mounting hole.

A cutting insert includes a main surface formed in a substantially parallelogram shape and having a pair of acute angle corner portions and a pair of obtuse angle corner portions, a seating surface that faces a side opposite to the main surface, a side surface that connects the main surface and the seating surface to each other, a corner cutting edge disposed in the acute angle corner portion, and a main cutting edge and a subsidiary cutting edge which are respectively disposed in a pair of side ridge portions of the main surface located each other across the acute angle corner portion. A mounting hole into which the fixing member is inserted penetrates the main surface and the seating surface. The main cutting edge is inclined at an inclination angle equal to or larger than 8 with reference to a plane perpendicular to an axial direction of the mounting hole.

A toolholder includes a bottom abutment surface, a projection extending upwardly from the bottom abutment surface, the projection including an internally threaded opening, having a central axis that is offset from a central axis of the projection in a first direction, and a clamping screw having external threads for mating with threads of the internally threaded opening and a head having a bottom clamping surface shaped as a truncated cone for contacting an insert clamping surface and urging an insert substantially in a first direction when the clamping screw is tightened relative to the toolholder and the insert. The toolholder also includes at least one abutment member extending from a side wall of the projection in a radial direction, each abutment member having an abutment point, at least which is closer to the central axis of the projection than to the central axis of the internally threaded opening.