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The substantial passage of wealth that occurs upon death in the United States each year brings into focus the tension between the belief that people should be able to dispose of their wealth as they wish and society’s interest in maintaining social stability. Nowhere is this tension more apparent than in the doctrine of undue influence. The dominant paradigm presents the undue influence doctrine as providing a double benefit of protecting freedom of testation as well as preventing overreaching by others. In this Article, the author challenges the dominant paradigm by demonstrating how the undue influence doctrine denies freedom of testation for people who deviate from judicially imposed testamentary norms - in particular, the norm that people should provide for their families. Part I looks at how case law, treatises and other authoritative sources describe undue influence as a doctrine that protects testamentary freedom. Part II studies the dominant paradigm more closely by looking at the application of the doctrine to a specific undue influence case. Part III explores the paradox of the undue influence doctrine. The doctrine purports to protect freedom of testation, yet, as Kaufmann illustrates, the standards for undue influence can be met even when the will reflects the wishes of the testator. Part IV tests this new paradigm of the undue influence doctrine as a family protection doctrine by looking at how the existence or nonexistence of other provisions protecting the family against disinheritance affects the operation of the doctrine. Part V concludes by exploring whether the undue influence doctrine can be justified once it is understood in terms of family protection, rather than as a doctrine committed to preserving freedom of testation.