It has long been recognized that legal documents are invaluable for understanding the growth of pre-university teaching across fifteenth- and sixteenth-century England; when surveyed as a whole, they allow the general spread of schooling to be mapped with precision. However, smaller, more scattered legal proceedings involving teachers can be no less suggestive. Late medieval and early modern masters submitted legal pleas on a range of issues, and found themselves accused of a striking array of crimes, including murder, assault, fraud, incompetence, theft, adultery, and even high treason. Such episodes have more than anecdotal value—they throw into relief many of the conditions in which teachers of the period operated. In particular, they provide clear insight into the economic realities of medieval and early modern teaching, showing the pressures, rivalries, and anxieties that overshadowed the lives of masters, and demonstrating that instruction was not staged in a social or political vacuum.