The multiclass prediction approach to the problem of recognizing the state of the drill by classifying images of drilled holes into three classes is presented. Expert judgement was made on the basis of the quality of the hole, by dividing the collected photographs into the classes: “very fine,” “acceptable,” and “unacceptable.” The aim of the research was to create a model capable of identifying different levels of quality of the holes, where the reduced quality would serve as a warning that the drill is about to wear down. This could reduce the damage caused by a blunt tool. To perform this task, real-world data were gathered, normalized, and scaled down, and additional instances were created with the use of data-augmentation techniques, a self-developed transformation, and with general adversarial networks. This approach also allowed us to achieve a slight rebalance of the dataset, by creating higher numbers of images belonging to the less-represented classes. The datasets generated were then fed into a series of convolutional neural networks, with different numbers of convolution layers used, modelled to carry out the multiclass prediction. The performance of the so-designed model was compared to predictions generated by Microsoft’s Custom Vision service, trained on the same data, which was treated as the benchmark. Several trained models obtained by adjusting the structure and hyperparameters of the model were able to provide better recognition of less-represented classes than the benchmark.