Can rabbis righteously bless meals containing non-kosher food? This centuries-old theological dilemma continues to challenge Jewish religious authorities, particularly as interfaith and secular celebrations become more common. Through careful analysis of classical Jewish legal sources—from Maimonides and Ravad to Jacob Ben Asher, Joseph Karo, and Moses Isserles—a clear pattern of scholarly debate emerges. While Ravad contended that blessings remain appropriate when benefit derives from consumption, Maimonides firmly opposed any blessing over forbidden foods. The preponderance of halakhic authority, including influential voices like Rashi and Isserles, ultimately supports the prohibition against blessing non-kosher food. Based on medieval and early modern textual analysis, the evidence indicates that rabbis should abstain from reciting ceremonial hamotzi blessings at meals containing forbidden foods, as such blessings inappropriately sanctify the entire meal and constitute a form of religious defiance. Such participation creates an irreconcilable theological contradiction that undermines the sacred nature of kashrut observance within Conservative Jewish practice.