This dissertation explores youth punishment in Canada in the social systems of law and education. It specifically focuses on three problems in the sociology of youth punishment: a gloomy state of theorizing; the absence of a more frontally distinct analysis of youth punishment beyond the realm of exclusion; and the underdevelopment of inter-systemic and intra-systemic features of youth punishment. This study confronts these issues with an exploratory qualitative analysis. The questions guiding this work include: how are youth punished in the systems of law and education? And, in the context of youth punishment, are the social systems of law and education linked, and if so, how? While many important contributions focus on the effects of punishment and what (over)determines punishment, my work addresses the absence of an empirical and theoretical understanding of youth punishment from the point of view of social systems. This project is different from other scholarship in the field as it relies on insights from Niklas Luhmann's contemporary social systems theory. This perspective allows me to foreground the inter-systemic and intra-systemic features of youth punishment in law and education. My research highlights the peculiarities of punishment in law and education and shows how punishment can connect social systems. I expose how there are distinctly educational and distinctly legal features of youth punishment. First, I present a suite of intra-systemic features of punishment in law. The peculiarities of youth punishment in law are captured with law's focus on protection, distinguishing fools from fiends, observing the character and consequences of youth behaviour, and pursuing accountability. Second, I show the features of youth punishment in education by documenting the locality of behaviour, school climate, and progressive discipline. Finally, I explore how systems influence each other, which means that law can productively make use of education and education can productively make use of law. My study foregrounds the day-to-day workings of legal and educational punishment and the interactions between these two social systems. This contribution shows that more attention could be paid to the social systems where punishment unfolds and the connections between social systems when punishing.