Abstract: A fresh look at Erasmus’ Institutio Principis Christiani – a work perhaps all too often neglected by critics – enables us to resolve the apparent contradiction of a text that advocates honesty, understood as liberty and sincerity, by practicing dissimulatio. As a speculum civis, Étienne de la Boétie’s Discours de la servitude volontaire represents an exercise in sincerity in which the reader must not only untangle the author’s intentions, but must also question his or her relationship with the Prince and figures of authority.