The article examines Ovid’s evaluation of Augustus’ political regime on the basis of the analysis of his interpretation of libertas. The aim of the research is to determine the key meanings of this concept through a detailed examination of the context of its use and to reveal the peculiarities of its semantic relations with the terms “licentia”, “lex”, “ius”, “pudor” and “metus” or “timor”. In the Republic era lex and ius were considered to guarantee political libertas and to prevent it from degenerating into its extreme form, licentia. The latter was understood as one of the signs of a degrading political system and a prerequisite for the establishment of slavery and tyranny, the reign of fear, violence, depravity and injustice. These ideas were refl ected in the poetry of Virgil and Horace who saw Augustus as a protector against such disasters. Unfamiliar with the hardships of civil wars, their younger contemporary Ovid was a bearer of diff erent values, sharply antagonistic to republican morality and many elements of the official ideology of Augustus’ principate. The concept of liberty he had implicitly formulated had a very defi nite political content and oriented the young generation of Romans towards resistance to specific aspects of the system of principate. The study has shown that the term “libertas” in Ovid’s writings is semantically close to the concept of licentia. In most of the cases studied, however, this category has positive connotations and means the possibility of love passion unleashing and the right to express obscene thoughts in private life. As far as freedom is concerned, Ovid demonstrates his dissatisfaction with the strictly republican features of Augustus’ rule. Leges and iura of the principate regime, which embodied the strict moral imperatives of the Republic era, not only did not guarantee freedom, but by provoking shame (pudor) and fear (metus, timor) severely suppressed it. Thus, they prevented achieving the most important value for Ovid — personal happiness (felicitas).