Insufficient coating adhesion limits reproducibility regarding tool lifetime as well as workpiece quality during the application of CVD-diamond coated cutting tools. Depending on the combination of tungsten carbide substrate material, coating thickness as well as coating morphology, individual residual stress conditions exist within CVD-diamond coated cutting tool specifications. The application of these tools is accompanied by coating delamination as primary cutting tool failure. The tool lifetime of the respective cutting tool composition depends on the corresponding residual stress condition until crack development within the CVD-diamond coating initiates tool failure. During external cylindrical turning of hypereutectic aluminium silicon alloy AlSi17Cu4Mg-T6 the residual stress condition of a CVD-diamond coated cutting tool is assessed along the cutting edge, the rake face as well as flank face throughout the respective tool lifetime. Consequently, the progression of the residual stress condition until cutting tool failure regarding coating delamination is observed. During the tool lifetime of the investigated CVD-diamond cutting tools, compressive residual stress ∆σR,c shifts to tensile residual stress ∆σR,t underneath the cutting edge corner. The approximated residual stress difference of ∆σR ≈ 5 GPa indicates stress peak relaxation processes, such as crack initiation, within the CVD-diamond coating.