With the abolition of the guild system and the rise of a new legal regime based on free contract, a central dilemma emerged in Europe: how to enforce labour control in this new era of individual economic freedom. This article examines how this issue was addressed in the State of Milan, where ideas about freedom of contract championed by state reformers such as Pietro Verri and Cesare Beccaria were met with continued requests from merchant-manufacturers to apply corporal punishment and threat of imprisonment to ensure workers’ attendance. Analysing the new regulations, the ideological credos of the new regime, and the effectiveness of the reforms as they played out on the ground in the silk industry, this article shows that the chance that labour relations could be managed within a civil law regime appeared to be in direct contrast with the dominant conception of workers’ conditions, in particular their lack of propriety and good faith. As credit-debt bonds and limitations to weavers’ mobility stood as the most effective means to ensure labour coercion, a closer look at the daily interactions in the workshop allows us to shed new light on the rationality of workers’ practices like Saint Monday, cast by contemporary commentators in merely moralistic terms.