The acceptance of the machined surfaces not only depends on roughness parameters but also in the flatness deviation (Δfl). Hence, before reaching the threshold of flatness deviation caused by the wear of the face mill,
the tool inserts need to be changed to avoid the expected product rejection. As current CNC machines have the facility to track, in real-time, the main drive power, the present study utilizes this facility to predict the flatness deviation—with proper consideration to the amount of wear of cutting tool insert’s edge. The prediction of deviation from flatness is evaluated as a regression and a classification problem, while different machine-learning techniques like Multilayer Perceptrons, Radial Basis Functions Networks, Decision Trees and Random Forest ensembles have been examined. Finally, Random Forest ensembles combined with Synthetic Minority Over-sampling Technique (SMOTE) balancing technique showed the highest performance when the flatness levels are discretized taking into account industrial requirements. The SMOTE balancing technique resulted in a very useful strategy to avoid the strong limitations that small experiment datasets produce in the accuracy of machine-learning models.