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This essay uses the case of a childless widow and her apostate brother-in-law to examine how gender and conversion became lightning rods for Jewish legalists and publicists like Moshe Leib Lilienblum to espouse religious and social reforms in late-imperial Russia. A microanalysis of Sura Gener's sensational levirate divorce case and the multiple legal regimes involved in adjudicating her fate sheds light on the history of Jewish modernization in the late Russian empire and argues that there was no straightforward process of secularization. In the crosscurrents of late nineteenth-century Russian Jewish social and religious life—Haskalah, Orthodoxy, government intervention, economic dislocation and migration, Jewish apostasy, and assimilation—women became a battlefield for the fight over changing religious and social norms and communal authority. Rather than a narrative of modernity entailing the weakening of halakhah, the decline of rabbinic authority, and a reactionary Orthodoxy, the Gener affair highlights the religious preservationist aspects of the Haskalah, the expansion and assertiveness of rabbinic authority buttressed by mass transport and new media, and the potential alignment of ritual expertise and social reform in rabbinic interpretation and vernacular debate. As such, analysis of the Gener affair adds a helpful corrective, exploring the paradoxical rise and creative development of religion at a time when standard models of secularization suggest that it should have declined.