Chip control is essential for the manufacturing with geometrical defined cutting edge to avoid interruptions of the process, damages on the machine or injuries of the machine operator. Hereby the prediction of the chip shape is highly relevant and scope of the present research work. High speed filming of the flowing chips, analyses of the contact zones between cutting tool and chip; as well as cutting simulations using the software DEFORM 3D™ are conducted to achieve an understanding of fundamental relations and the effectiveness of different chip groove geometries. A newly developed web-based expert system searches for similar datasets in a database with captured applications and is furthermore able to predict the chip shape for a planned application. Therefore the chip breakage borders for many tool-material-combinations are determined empirically and captured in the database. The software judges by these borders, if for a certain parameter set point, either chip breakage or unfeasible chip shapes occurs. Inter- and extrapolations for so far unknown datasets are also based on the borders. These operations are operating with correction values and the data output is combined with a declaration of the output accuracy. Beside the search for similar applications and the prediction of chip breakage, the expert system is also capable to evaluate the effectiveness of chip groove geometries of cutting tools.