A cutting tool has a cutting insert retained in an insert pocket by a retaining screw. The rear surface of the cutting insert has an insert engaging element that comprises first insert rear abutment surfaces that are spaced apart and make an insert engaging angle with each other. The rear surface of the insert pocket has a pocket engaging element that comprises first pocket rear abutment surfaces that make a pocket engaging angle with each other. In a retained position, the first insert rear abutment surfaces abut the first pocket rear abutment surfaces, second insert rear abutment surfaces abut second pocket rear abutment surfaces and insert lower abutment surfaces abut pocket lower abutment surfaces.