Constitutional ambiguity and conflicting judicial precedents have created a legal quagmire surrounding the enforceability of the ketubah - Judaism's traditional marriage contract - in American civil courts. The tension is particularly acute regarding Conservative Judaism's addendum requiring cooperation in obtaining a get (Jewish divorce). Analysis of recent court decisions, correspondence with Talmudic authorities, and examination of legislative developments reveals stark jurisdictional inconsistencies. In Minkin v. Minkin, a New Jersey Superior Court asserted constitutional authority to enforce get provisions, viewing them as secular contractual obligations outside First Amendment constraints. Yet in Avitzur v. Avitzur, New York's Appellate Division rejected enforcement, deeming the ketubah a "liturgical agreement" beyond state purview post-civil divorce. Beyond civil law challenges, the research identifies significant halakhic concerns regarding asmakhta (conditional obligations) in Conservative addenda, proposing alternative prenuptial agreements with fixed liquidated damages as a potential solution. While Orthodox organizations have gained increasing influence in shaping legislation around religious impediments to remarriage, predictable ketubah enforcement remains elusive due to varied constitutional interpretations - a situation that raises broader questions about Jewish denominational representation in American civil law.