Is it ever moral to lie or deceive? Despite biblical prohibitions against lying, the Bible rarely offers an evaluation of its characters or their conduct, thus leaving the moral ambiguity regarding the Bible's attitude toward the ethical nature of deception open to interpretation by the reader. This article uses contemporary moral debate to elucidate the ethical problems that arise from morally ambiguous biblical narratives depicting deception. Did Abram, and later Isaac, act ethically when they identified their wives as their sisters? Were Simeon and Levi morally justified in their deception and ambush of the inhabitants of Shechem? Philosophical analysis of the biblical stories, in light of arguments advanced by Immanuel Kant and Benjamin Constant, support different interpretations that contribute to an enhanced understanding of the biblical text and a more informed evaluation by its readers.