The transformation of American Judaism's approach to conversion represents a crucial frontier in the religion's adaptation to modern pluralistic society. Dr. Gary Tobin's controversial 1999 proposal for organized Jewish proselytizing campaigns ignited an intense debate that continues to divide denominations and challenge traditional boundaries. Through analysis of rabbinic literature, demographic data, and contemporary religious discourse across Orthodox, Conservative, and Reform movements, a stark denominational divide emerges: Reform and some Conservative leaders advocate for proactive outreach while Orthodox authorities maintain restrictive traditional positions. Rising intermarriage rates, declining conversion percentages among non-Jewish spouses, and increasing assimilation have intensified questions of how Jewish communities should define and maintain their boundaries. The historical evolution of Jewish attitudes toward conversion, from ancient practices through modern American Judaism, reveals recurring tensions between preserving traditional Jewish law and responding to demographic pressures. While proponents view organized proselytizing as vital for both demographic survival and spiritual renewal, critics argue for prioritizing Jewish education within existing communities. These debates ultimately illuminate fundamental questions about Jewish identity, religious authority, and communal continuity in late twentieth-century America.