This chapter examines the fate of trans-Gibraltar region during Spanish Civil War and the early stages of World War II. Although the insurgent army of Francisco Franco quickly took control of northern Morocco and southern Spain and invited its Nazi and Fascist allies to the strategically crucial region, the Entente order of 1904 proved resilient. New evidence is introduced detailing the Franco movement’s success in marshaling anti-French, anti-Semitic, and pro-German sentiments to recruit Muslim support, promising the construction of a new Hispano-Moroccan bulwark in the western Mediterranean. Other new documents indicate how quickly this enthusiasm cooled, however, as it became clear that Nazi agents were preparing to seize a position in northwest Africa without giving consideration for Spanish interests, while the British and much of the Jewish community of Tangier remained supportive of Spanish interests in Morocco.