Recent scholarship on fate and free will in ancient Judaism is characterized by a lack of precision with regard to the nature of these disputes. There is also some disagreement concerning the degree to which the disparate positions can be constructively compared with either Hellenistic philosophical approaches or later rabbinic theological ones. It is argued here that Josephus's brief typology of ancient Jewish disputes on this topic finds confirmation in other ancient Jewish literature, especially the Wisdom of Ben Sira, the sectarian Dead Sea Scrolls, and later rabbinic literature. Yet it is imperative to nuance Josephus's typology so as to avoid imposing Hellenistic philosophical systems onto ancient Jewish theological ones. These observations hold true especially when it comes to understanding the balance between fate and free will — the “compatibilism” — that characterizes the Pharisaic approach. It is rarely noticed that Josephus's accounts attribute to this group two distinct ways of balancing fate and free will. On the one hand, each of these two approaches finds distinct analogues within rabbinic literature, a fact that further confirms both Josephus's reliability and the productivity of comparing his accounts with later rabbinic traditions. On the other hand, neither of the two types of compatibilism attributed by Josephus to the Pharisees can be identified with Stoic compatibilism. Nonetheless, the term “compatibilism” remains the most appropriate term for distinguishing the Pharisaic compromises from the more extreme (but by no means uncomplicated) positions that seem to have characterized the Sadducees and Essenes in Josephus's day.