Since its founding, the United Israel Appeal (UIA)—the longtime chief conduit of American Jewish giving to Israel—has passed billions in charitable dollars to support Israeli societal development but withheld support for charitable projects in the areas occupied by Israel during the 1967 War. While the UIA asserted that its reasons for this policy were U.S. law and government pressure, evidence suggests that it was not so simple. The article details the history of the UIA's Green Line policy and examines its likely motivations and implicit and explicit reasoning. Specifically, it focuses on the activity of one pro-settlement activist group that challenged the policy, claiming the UIA's justifications were exaggerated, if not fabricated. The UIA refuted this critique and stood by its policy and stated reasoning. The article explores the motives behind the UIA Green Line policy and questions why its justifications which were often less than forthcoming. It concludes with some reflections on the long-term legacies of UIA policy, and communication strategies on philanthropy, American Jewish identity, and Israel-diaspora relations.