William Shakespeare, like many other Elizabethans, took note of the fundamental change in the use of schoolbooks during the sixteenth century: from being rare teachers’ copies in the Middle Ages, schoolbooks became the common learning tools of schoolboys in early modernity. This article examines the timing of this change, its causes, and its far-reaching implications. Taking a book-history approach, this article argues that English grammar-school pupils started to learn with their own books in a gradual process taking place between 1510 and 1540. Following this process from edition to edition exposes the interplay of the material, intellectual, and commercial factors that shaped early modern education. Once every schoolboy sat in school with book in hand, the structure of schooling, the role of the teacher, the course of the lesson, and the cognitive aspects of learning went through deep shifts. This in turn affected early modern culture in profound, often surprising ways.