The constant need of researchers for the advanced study of the problems of guilt and responsibility is caused both by the tasks of improving legislation and law enforcement practice and the variability of people’s ideas about the grounds, limits, forms, and purposes of personal responsibility, and ideas reflecting the actual process of the historical development of social relations and the practice of their legal regulation. Using the methods of historical-legal and comparative-legal analysis, the author studied the activity of the legislator on distinguishing the intent and negligence as two forms of guilt when committing transport offenses, as well as differentiating between guilty infliction of harm and an incident. The author concluded that in the sources of Russian law of the 16th-19th centuries, the legislator strongly focuses on the internal (subjective) attitude of a person to a committed offense and its consequences, including transport offenses. The discovery and consideration of such signs of the subjective aspect of an act as guilt, motive, and purpose significantly influenced the act classification and the punishment appointment or led to release from liability due to the absence of the subjective aspect of an offense (guilt) as one of the elements of a crime. The study shows how the legislator considered the influence of a person’s subjective attitude to the committed act when establishing legal responsibility. The research indicates that a comprehensive understanding of guilt as an integral characteristic of a wrongful act, covering the relations between consciousness and will of a person both with the objective properties of own actions and its public assessment, began to develop in Russian law in the 17th century.