How do we even think about the Roman elegist Propertius in light of Augustus, Rome’s first emperor, whose relationship has been the subject of much controversy? Propertius’ family lost its estate and status, and his region suffered terrible reprisals, as punishment for having been loyal to Mark Antony against the future ruler Augustus, and the poet’s resentment is evident in his work, despite the generous patronage of one of Augustus’ chief advisors. But his poetry is more subtle and complex than simple protest, and it evolved into further complexities as Augustus solidified his hold on Rome and Roman imperial holdings. How do elegy’s generic focuses on gender, social class, poetry, politics, power, and sex allow Propertius to work through his attitudes toward his nation and the ways it changed under monarchy? The talk will also consider the way Propertius’ attitudes toward Augustus and the Augustan settlement have been received in different periods, with some focus on the problems of artistic freedom in autocratic regimes.