Without continuous improvement of cutting-solutions in a machine-shop, the company is bound to become less competitive over time. Cutting tool manufacturers are always working to improve their products and the companies that adopt the improved solutions will be at an advantage. However, wear of the machines might prove to be a severe limitation to which tool selection strategies that can be used, and the path to a superior solution is not always a straight forward path. Mechanical error movements are of detriment to both workpiece-accuracy and tool-life and might rule out some solutions altogether. Since it’s not always economically feasible to address this type of error movements due to expensive spare-parts or costly downtime, some optimizations must be made with the wear in mind. This study aims to optimize a drilling operation without addressing the error movements performed by the machines.