The optimization of locomotive drivers’ scheduling in rail freight transportation comes as a necessity for minimizing economic expenses and training investments. The Ferodata AI engine, an artificial intelligence (AI)/machine learning (ML) software module, developed by our team, has integrated a supervised random forest model that automatically assigns conductors to freight transportation orders based on the data about locomotive driver’s tiredness score, distance of the driver to the departure point of a transportation order, driver availability, and circulation history. The model proposed by us obtained very good performance metrics on the train set (accuracy: 95%, AUC: 0.9905) and reasonably good and encouraging performance on the test set (accuracy: 84%, AUC: 0.8357). After rigorous testing and validation on external and larger datasets, the automated optimization of locomotive driver assignments could bring operational efficiency, cost savings, regulatory compliance, and improved safety to scheduled rail freight transports.