This chapter makes the case for “Global Haskalah,” an expansion and revision of Jewish literary history that investigates connections among Haskalah projects throughout the Jewish world as well as relationships between Hebrew and Jewish vernacular languages. While focusing on multilingual Jewish literary circulation and exchange in the global Jewish diaspora, my approach also emphasizes translation and rewriting as its primary mode of expression; the role of Hebrew as a mediator of intra-Jewish exchange and bridge from foreign languages to Jewish vernaculars; the relationship of Jewish literary revival to global trends and forces; and the colonial dynamics of world literature vis-à-vis the Haskalah. After outlining the Global Haskalah as a historical phenomenon and a scholarly methodology, I offer summaries of two case studies based on novels that circulated within Hebrew, Judeo-Arabic, Ladino, and Yiddish. The first, Robinson Crusoe, illustrates the strategies used by Jewish translators in domesticating a quintessentially European Christian text while the other, The Love of Zion, demonstrates the mix of cultural diversity and diasporic interconnection exemplifying the Global Haskalah. In both cases, I show how tracing routes of circulation, juxtaposing multiple Jewish-language translations, and reading them comparatively and contextually can generate new insights into the formation of Jewish literary modernity.