In his Life of Moses, Philo of Alexandria retells the biblical events of Moses’ life. Although his retelling is sometimes said to have paraphrastic qualities, there has not been a thorough scholarly attempt to compare it with examples of Greco-Roman paraphrase. This paper sets out to analyze Philo’s retelling of the biblical text in Mos. in light of the cultural production of such texts. By analyzing paraphrase both in its theoretical setting in rhetorical handbooks (e.g., Aelius Theon’s Progymnasmata, Quintilian’s Institutiones, and Aphthonius’ Progymnasmata) and in actual literary works, we may arrive at a typology of its essential characteristics, typical compositional techniques, and its common effects. Significantly, such an investigation reveals that Mos. has much in common with ancient paraphrases. By analyzing Mos. in light of ancient paraphrase, not only do we understand the text in a new way, but we also reveal more about Philo’s place in the wider literary culture. His reworking of the Exod 14 account of the parting of the Red Sea provides an excellent place to see Philo’s paraphrastic techniques at work. Exod 14 contains a narrative of the parting of the sea that has proved exegetically problematic for interpreters throughout the centuries. In particular, the plot sequence appears convoluted and several ambiguities present themselves to the reader. By surveying the reception history of the passage, three issues stand out prominently. First, the narrative purpose and function of Moses’ staff is unclear. Second, the sequence of events—particularly in how Moses’ staff and the wind work together—that leads to the splitting of the sea is confusing and somewhat illogical. Third, the manner in which the sea closes again could provide some potential problems. Like other exegetes, Philo is confronted with these same issues. Unlike other exegetes, however, by employing the methods of paraphrase, Philo deals with them not in an explicit manner but in an implicit way through crafting a new narrative. He does this in three ways. First, in his retelling of the event, he crafts a new narrative that resolves potential ambiguities and problems in the exemplar. Second, he improves the narrative coherence by rearranging the plot sequence. This also creates a more logical, plausible account. Third, he provides a narrative that contributes to his literary aim. Significantly, because he narrates the parting of the Red Sea twice in Mos., the episode provides a unique opportunity to see how Philo employs paraphrastic techniques. Both versions are contained in larger sections of the text that highlight certain features of Moses’ character. In his first telling, Philo aims to portray Moses as the ideal leader. In his second version, he aims to depict Moses as a prophet. As a result of these literary aims, as he resolves various issues in the biblical exemplar, he does so in such a way that he also contributes to his literary aims of depicting Moses as leader or prophet.