Employing novel data on over 400 apprenticed orphaned boys from the Dutch cities of Leiden and Utrecht, this article explores the functioning of apprenticeship during and after the guilds. Although the mobility of apprentices was high and contracts were uncertain, no complaints arose from masters or guilds. Wages paid to these apprentices demonstrate that their labour made a gradually increasing contribution to the workshop from the start of their term. This enticed masters to take on apprentices and removed the need for contract enforcement. After the guilds were abolished, the number of apprenticed orphans in the crafts grew, suggesting that guilds previously hampered access to training. Additional data collected for regular (non‐orphan) apprentices corroborates these findings.