To date, we have two translations of the Conferences of John Cassian in Old French, for each of which just one manuscript has been preserved. One was made by Jean Golein by order of Charles V and is dated 1370, while the other, commissioned by Edward I of Portugal, is the work of an anonymous scribe, and generally agreed to have been composed between 1391 and 1438. This study examines the translation strategies necessitated by a change of readership, from monks for the original text to a courtly audience for the translations; by the still very intense issues around the subject of Pelagianism; and by the development of attitudes about the scale of vices, and particularly in the case of the present text, of gastrimargia, castrimargie, and even gloutonie. Each of these two popularizers accepted these challenges and molded them according to their own world.