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This self-study explores the challenges I face as a Jewish professor integrating Jewish perspectives into diversity education amid politically sensitive topics like the Israeli-Palestinian conflict. As a Jewish Ashkenazi woman from an upper middle-class background, I have hesitated to disclose my Jewish identity due to fears of bias. Institutional silence and a lack of inclusive spaces compound these concerns. The study identifies barriers such as antisemitism, biased student reactions, safety concerns, and emotional labor. Using the HebCrit framework, it aims to address these obstacles and develop strategies for overcoming barriers. Findings highlight the urgent need for greater institutional support, self-identity development, and professional development to create an inclusive environment where diverse identities are respected.