A cutting tool, comprising at least one cutting portion, the at least one cutting portion comprising an insert pocket having a cutting insert releasably retained therein, wherein the cutting insert has a top surface, a bottom surface, and a peripheral surfaces extending therebetween, the peripheral surface comprising two opposing major sides and two opposing minor sides; the bottom surface comprises a plurality of engagement surfaces, of which a plurality of operative engagement surfaces engage an attachment surface of the insert pocket in a respective plurality of sloping and non-sloping engagement regions; the plurality of operative engagement surfaces comprising; first and second spaced apart operative sloping surfaces (34', 36'), whose respective sloping engagement regions (80, 82) lie in a first plane forming an acute angle (α) with a first median plane (M 1) of the cutting insert; an operative inner sloping surface whose respective inner sloping engagement region lies in a second plane forming an obtuse angle (β) with the first median plane (M 1), the acute and obtuse angles (α, β) being measured in the same direction from the first median plane (M 1); and operative first and second corner surfaces (40', 42') whose respective non-sloping corner engagement regions (72, 74) lie in a third plane that is substantially perpendicular to the first median plane (M 1) and to a second median plane (M 2) of the cutting insert, the second median plane (M 2) being perpendicular to the first median plane (M 1), wherein the operative first and second sloping surfaces (34', 36'), and the operative inner sloping surface are located on a first side of the first median plane (M 1), and the operative first and second corner surfaces (40', 42') are located on a second side of the first median plane (M 1); characterized in that the first and second operative sloping surfaces (34', 36') are located at opposite sides of the second median plane (M 2), and wherein the operative inner sloping surface intersects the second median plane (M 2); and in that the first and second spaced apart operative sloping surfaces (34', 36'), the operative inner sloping surface and the operative first and second corner surfaces (40', 42') are the only surfaces on the cutting, insert having engagement regions in abutment with the attachment surface of the insert pocket. an insert pocket having a cutting insert releasably retained therein, wherein the cutting insert has a top surface, a bottom surface, and a peripheral surfaces extending therebetween, the peripheral surface comprising two opposing major sides and two opposing minor sides; the bottom surface comprises a plurality of engagement surfaces, of which a plurality of operative engagement surfaces engage an attachment surface of the insert pocket in a respective plurality of sloping and non-sloping engagement regions; the plurality of operative engagement surfaces comprising; first and second spaced apart operative sloping surfaces (34', 36'), whose respective sloping engagement regions (80, 82) lie in a first plane forming an acute angle (α) with a first median plane (M 1) of the cutting insert; an operative inner sloping surface whose respective inner sloping engagement region lies in a second plane forming an obtuse angle (β) with the first median plane (M 1), the acute and obtuse angles (α, β) being measured in the same direction from the first median plane (M 1); and operative first and second corner surfaces (40', 42') whose respective non-sloping corner engagement regions (72, 74) lie in a third plane that is substantially perpendicular to the first median plane (M 1) and to a second median plane (M 2) of the cutting insert, the second median plane (M 2) being perpendicular to the first median plane (M 1), wherein the operative first and second sloping surfaces (34', 36'), and the operative inner sloping surface are located on a first side of the first median plane (M 1), and the operative first and second corner surfaces (40', 42') are located on a second side of the first median plane (M 1); characterized in that the first and second operative sloping surfaces (34', 36') are located at opposite sides of the second median plane (M 2), and wherein the operative inner sloping surface intersects the second median plane (M 2); and in that the first and second spaced apart operative sloping surfaces (34', 36'), the operative inner sloping surface and the operative first and second corner surfaces (40', 42') are the only surfaces on the cutting, insert having engagement regions in abutment with the attachment surface of the insert pocket.