Jewish identity through matrilineal descent - a cornerstone of traditional Judaism - rests on rabbinic interpretations that warrant fresh examination in our contemporary era. The traditional reading of Deuteronomy 7:3-4, which interprets "your son" as "your grandson" to establish maternal lineage as determinative, raises significant hermeneutical questions. Through comparative analysis of biblical and talmudic sources, this research traces how Jewish authorities historically adapted halakhic principles to changing social conditions, particularly evident in the liberalization of conversion laws and the modification of biblical prohibitions against Ammonites and Moabites. The study examines pivotal historical precedents, including the intermarriage crisis documented in Ezra and Nehemiah, demonstrating Judaism's capacity for legal evolution. Building on the principle of *zera kodesh* and Rabbi Dimi's teachings on marital fidelity, this analysis proposes extending Jewish status to children of Jewish fathers and non-Jewish mothers - a particularly urgent consideration for Jewish emigrants from communist countries where paternal legitimacy can be reasonably presumed. While acknowledging the gravity of Jewish legal authority, this research advocates for halakhic courage in addressing modern realities, offering a framework for principled evolution within Jewish law.