This article deals with a mutual comparison of indexable cutting inserts of the CNMG 120408 type from two different manufacturers during the machining of hardened steel AISI 4337 and austenitic stainless steel AISI 316 L. The main goal is to analyse the different wear processes depending on the difference in the manufacturer’s design and also depending on the properties of the different machined materials. The progress of the wear of the main spine of the tool, the types of wear and the service life of the cutting edge were monitored, with the achievement of the critical value VBmax = 300 µm being the standard. In addition to the wear of the inserts, the production of chips was monitored in terms of their shape, average size and number of chips per 100 g of chips produced. In order to understand the relationships arising from the obtained data, an SEM equipped with an elemental analyser was used to analyse the coating layers and the substrate of the unworn inserts and the types of wear and the intensity of the surface damage of the worn inserts. A several-fold difference in the lifetime of the cutting edge was found, both in terms of design and in terms of the selected machined material, while in both cases the cutting edge with Al2O3 and TiCN layers of half thickness achieved a better result in liveness. From the point of view of chip formation, very similar results in shape and average length were observed despite the different designs of chip breakers. Cutting inserts with half the thickness of the coating layers achieved longer cutting edge life in the non-primary material application compared to the target workpiece material. At the same time, it was observed that a thinner coating layer has a positive effect on chip formation in terms of its length and shape.