Texts from the Tannaitic midrashim and the New Testament show that slavery and freedom were ambiguous states-of-affair for the ancient Jews and Christians; it depended on the slave’s source (e.g. debt or war) and the kind of master (a fellow-countryman and fellow-believer, versus a ultimate pagan foreigner) how the state of slavery was evaluated. By a close reading of a hitherto unexplored parable from Sifre Numbers (parasha 115) I will clarify the paradoxical way in which the early rabbis thought about slavery - that at the same time becoming a slave of God was the purpose of the people of Israel, while being a slave of Egypt’s ruler was its ultimate degradation. In the New Testament letters of Paul we encounter similar ideas: Christians should liberate themselves from sins, not in order to become free, but in order to become slaves of God (Romans 6:20-22). This theological discourse also had its imprint on social reality. On the basis of halakhic discussions in the Babylonian Talmud I will argue that although slavery was taken for granted, it was encouraged in early Rabbinic Judaism to redeem Hebrew slaves from foreign slavery - not in order to be freed, but in order to serve in Israel, under Jews and under God. In this way, this paper will make clear how the early Rabbinic and early Christian discourse on freedom and slavery is at times both puzzling and paradoxical, but rarely illogical.