Abstract American law is notoriously solicitous of property owners’ testamentary freedom. Interpretive theorists cannot but acknowledge its centrality to enabling law. Yet freedom of testamentary disposition has attracted criticism on normative grounds for centuries. Indeed, it is widely viewed as one of the most tenuous of incidents of private ownership. This chapter examines leading defences of testamentary freedom and, finding them lacking, offers an alternative. Viewed within conventional frames of the general morality of property, wide testamentary freedom proves difficult to justify. Arguments from property, autonomy, social utility, and an obligation of provision each fail to ground laws enabling testamentary freedom. This chapter argues that testamentary freedom is better defended on the footing of the morality of gift relationships, with particular attention to the value of testamentary benefaction in enabling the expression of moral motivation, the practice of virtue, and realisation of goods essential to human flourishing. An advantage of this approach is that it recognises moral complexity, allowing one to appreciate the value of dispositions that comport with the focal moral sense of benefactions as gifts, while at the same time pinpointing ways in which other dispositions can prove morally defective despite their legal validity.