This is a term used to refer to the students at a preparatory school. The phrase derives from the fact that students at preparatory schools are not “day students” (i.e., students who go home each night) but “boarding students” who live at a school for an entire term. Orwell is highly critical of this process in his essay, and he suggests that boarding itself is largely responsible for much of the misery and neglect suffered by students of St Cyprian’s. Isolated from their families, the school becomes their entire world.

A headmaster was a lead administrator of a school, whether in preparatory (lower) or public (higher) education. The role not only demanded the typical administrative functions comparable to modern school principals but also entailed teaching classes and taking direct responsibility for all disciplinary matters at a school. The headmaster of St Cyprian’s (nicknamed “Sambo” in Orwell’s essay) is presented as typical of his profession, being primarily interested in the prestige and financial success of his institution. Orwell suggests such motivations as being inherent to the position.

Preparatory schools in Britain were created to prepare wealthy young men for entrance exams into prestigious public schools. St Cyprian’s (the school featured in the essay) is one such school, and Orwell reveals through his anecdotes the practices that existed within such institutions.