As a consequence of the 17 April 1905 law on religious freedom, hundreds of baptized Jews petitioned to return to Judaism. While the law paralleled the liberalization of the attitudes and values regarding religious differences that occurred in European societies between the sixteenth and twentieth centuries, the reform also helped destabilize traditional social boundaries and religious identities in the empire. On one level, this essay examines the conflicts and problems authorities faced in categorizing a Jewish population that continually resisted conventional assumptions. In the context of rapid population movements, political and religious reforms, and increased acculturation, what it meant to be “Jewish” was redefined, and administrators needed to establish an acceptable criterion by which (baptized) Jews could be classified. On another level, this essay draws on individual petitions and government correspondence to analyze the personal choices and social dilemmas that baptized Jews faced when they attempted to return to Judaism.