Josephus attests several times to a Jewish aversion to the use of Gentile olive oil. In m. ‘Abod. Zar. 2:6, this practice is first advocated and then immediately reversed by Rabbi and his court. What is the rationale for this sudden leniency with regard to Gentile olive oil? In a well-known article entitled “Kosher Olive Oil in Antiquity,” Martin Goodman argues that Rabbi’s statement is the result of his inability to find a legal basis for the prohibition of Gentile olive oil. Goodman, however, accounts neither for the unique economic and dietary factors associated with olive oil, nor tannaitic legislation regarding other foodstuffs that may shed light on this case. In this article, I reconsider Jewish stances towards Gentile olive oil in antiquity from the time of Josephus to the Tannaitic period.