Since its inception, scholars of the nineteenth-century Wissenschaft des Judentums or “Science of Judaism” movement have had a complex relationship with the discipline of Orientalism. As a diasporic religious community whose geographic and cultural settings have varied widely over millennia, Jews and their faith traditions have been classified on both sides of the Oriental/Occidental dichotomy, and such classifications have always carried political and social connotations, implicitly or overtly. Likewise, the role of contemporary Jewish or Judaic Studies in the study of the so-called Near East, MENA, or SWANA – and vice versa – remains a fraught topic, wrapped up in identity, emotion, and ongoing political considerations. To put the point starkly, the Jewish religion arose in ancient Mesopotamia, Egypt, and the Levant, and Jews in subsequent epochs settled across the SWANA region from India to Morocco, an area that contained the majority of Jews until the early modern period. Even then, Jews in Europe maintained connections to their Sephardi/Mizrahi co-religionists and were often perceived by their non-Jewish neighbors as “oriental.” Yet the study of Jews and Judaism, and that of SWANA religions, histories, and politics, have often proceeded independently of one another, with little dialogue between respectively-situated scholars. Perhaps no area is more crucial for examining and addressing problems in the development of these disciplines than that of pedagogy. It is in the classroom that students’ pre-existing understandings (and misunderstandings) are either reinforced or reconfigured, and where instructors can explain the historical boundaries of their fields and offer more inclusive frameworks for training future generations of scholars and informed members of diverse societies. The inclusion of Jews and Judaism within SWANA Studies on one hand, and the inclusion of SWANA Studies within Jewish Studies on the other, are not without serious, ongoing challenges. Jews continue to identify, or be identified, with different cultural affiliations in different contexts, or for different purposes. And the unresolved conflicts pertaining to Israel-Palestine mean that many of these issues are far from theoretical but relate directly to ongoing political violence and discrimination. While vital, these classroom conversations risk becoming unproductive – or worse – if not thoughtfully framed and conducted. In this paper I survey some of the challenges and opportunities for integrating Jewish Studies and SWANA Studies in various classroom settings, and I discuss my own experiences as well as those of colleagues and collaborators.