The late nineteenth-century conversion of Jews to Russian Orthodox Christianity was complicated and contested. Anti-conversionist sentiment and popular anti-Semitism, both fueled by skeptics of "conversions of convenience," threatened to undermine the missionary effort and forced the Church to reevaluate the old question: can Jews be converted to Christianity? The resurrection of this debate, paired with increasingly low conversion rates and poor religious observance among Jewish converts, created a crisis within the missionary enterprise. Orthodox missionaries to the Jews, facing an increasingly ambivalent Church and an anti-Jewish parish, sought to revitalize their conversion methods and find new ways to strengthen the faith of recent converts. One way in which they did this was to employ former Jewish converts who could explain Russian Orthodoxy to potential converts, and Judaism to skeptical Russian Orthodox Christians. This research project will analyze how Orthodox missionaries adapted their proselytization techniques to quell popular anti-conversionist sentiment in the turbulent post-reform decades (1860-1890). In this vein, it will explore one response to the "convertibility" question: the decision to employ Jewish converts as missionaries to the Jews. It will ask several key questions. First, how did the converts impact missionary discourse and the conversion effort? Second, what was the reception of their work: how did Jews and Russian Orthodox Christians read and react? How did the converts differentiate between ethnicity and confessionality? Did they consider themselves simultaneously Jewish and Christian? How did others define them?