In the midst of a larger dispute with Prague’s first coffee-boiler, Rabbi David Oppenheim was accused of overseeing the transfer of money from the Habsburg Empire to Jewish communities in the Land of Israel (which was under Ottoman rule). In the fraught atmosphere of the Counter-Reformation and the Ottoman-Habsburg wars, this Jewish practice was cast as treasonous; it not only drained money from state coffers but also transferred it to an enemy land. This article examines the trial against Oppenheim, exploring intimations of Jewish-Turkish collusion and paying particular attention to the “Jewish money-transfer affair” and its repercussions. This article also explores subsequent debates and controversies about the collection of funds in the Habsburg Empire for distribution in the Land of Israel.