Most people are familiar with loopholes. When your boss, landlord, partner, customer, or government asks you to do something you don’t want to do, and yet you can’t say “no,” you may resort to malicious compliance – doing what someone asked, but not actually what they meant. Most parents are probably familiar with such “little lawyer” behavior too: if a parent says, “Time to put the tablet down,” a child might physically put the tablet down on the table – and then keep playing on it. While such intentional misunderstandings are common and important, there has been little research on the development of loophole behavior across childhood. In a new Child Development study from the Society for Research in Child Development (SRCD), researchers at the Massachusetts Institute of Technology and Harvard University examined when and why children engage in loopholes. Tracing the origin of loophole behavior and how communication goes wrong can help us to better understand how communication often goes right, when people are motivated to cooperate. This may be the first research to explore the phenomenon of loopholes across development and can help contribute to a broader understanding of social reasoning.