Focusing on the manumission scenes, the article radically revises current understanding of the role of freedom in the so-called Cena Trimalchionis. Through detailed analysis of each of the tree scenes, I demonstrate that the traditional understanding of the host’s increasing loss of control is mistaken, raising furthermore doubts over the notion of unpredictability in the reading process. The analysis also demonstrates the significance of the variety of freed statuses in imperial Rome for our understanding of slavery and freedom at Rome. Finally, the newly gained insight into the depiction of varied freed statuses in the Cena enables a fresh comparative view with other texts of the imperial period that engage with freedom and slavery. One such comparative angle is followed up in the article, regarding a set of letters of Pliny the Younger: this comparison enables in conclusion a better understanding of the date of composition of the Cena, removing it from its traditional Neronian dating, and demonstrating a new terminus post quem of AD 115. The article is essential reading for the study of Roman slavery, Roman social history, and the literature of the Roman Empire, both Latin and Greek, especially of the period often referred to as the Second Sophistic.