The TiAlCrSiYN-based family of physical vapor deposition (PVD) coatings were systematically designed through the incorporation of TiAlCrN interlayer to increase coating adhesion and consequently the tool life for extreme conditions that arise during dry high-speed milling of hardened tool steels. The investigation in the present paper intends to explain the effect of TiAlCrN interlayer thickness on the overall coating properties and cutting performance. A comprehensive characterization of the structure and properties of the coatings has been performed using focused ion beam (FIB), scanning electron microscope (SEM), X-ray powder diffraction (XRD), nanoindentation, ramped load scratch test, repetitive load wear test, and nano-impact test. The wear test at a subcritical load of 1.5 N showed that there was a gradual improvement in coating adhesion to the substrate as the interlayer thickness increased from 100 to 500 nm. However, the wear performance, being related to the ability of the coating layer to exhibit minimal surface damage under operation, was found to be associated with micro-mechanical characteristics (such as hardness, elastic modulus). Around a 40% increase in the cutting performance with 300 nm interlayer exhibited that a substantial increase in tool life can be achieved through interlayer thickness variation, by obtaining a balance between mechanical and tribological properties of the studied coatings.