This study investigates tannaitic material and passages from the Jerusalem Talmud that address the integration of the descendants of converts into Israel. These texts focus on two main legal issues: the eligibility of converts’ daughters for marriage with priests; and, the recitation of certain liturgical formulae, which indicate Israelite lineage, by converts’ offspring. While tannaitic literature presents competing views on the incorporation of converts’ progeny into Israelite society, the Yerushalmi seems to prioritize facilitating the absorption of converts and their descendants into Israel. While scholars have often considered these sources in terms of stringency and leniency, I view these differences as major (even revolutionary) changes that are based on distinct legal models. I suggest that the Roman understanding of citizenship and the Roman framework for determining the status of freed slaves were among the factors that influenced and eventually enabled the acceptance of converts’ descendants as full members of Israel.