This article explores trade guilds in early modern Madrid in light of the revisionist stream of research that has enriched our understanding of these institutions in the European context. It focuses on the relationship between governmental regulations, the evolution of guilds, and the changes in the industrial structure of the city, relying on information gathered from guild ordinances, tax rolls, and most importantly, over ten thousand master licenses and three thousand indenture contracts for fifty-three craft guilds. The analysis of this data set shows that the reproduction of Madrid’s guilds did not only depend on father-to-son transmission but rather on the admission of nonkin and immigrant workers. Contrary to previously held ideas about corporate rigidity and closed guilds, this study reveals a diverse and flexible guild system in which norm and practice did not always go hand in hand. We contend that despite their limited autonomy, guilds were able to create their own artisan labor markets due to the political control inherent in a court city. The long-term approach to the evolution of both apprenticeships and masterships in Madrid—covering from the mid-seventeenth century to the end of the eighteenth century—has allowed us to establish comparisons with other European cities.