American Jewish religious organizations face a mounting contradiction: they oppose government funding for religious institutions while simultaneously accepting tax exemptions and military chaplaincy support. Through analysis of recent court decisions and organizational positions, particularly a Conservative congregation's tax liability case in Roslyn, Long Island, deep inconsistencies emerge in how major Jewish organizations navigate church-state boundaries. While these groups maintain strong opposition to direct financial aid for parochial education, they readily benefit from various tax advantages and religious accommodations. The expansion of Jewish day schools and deterioration of public education have prompted many organizations to reconsider their traditional strict separationist stance. This shift reflects broader tensions within Conservative Judaism as it strives to maintain halakhic continuity while adapting to modern circumstances. Critical examination of court decisions, organizational documents, and policy positions reveals that both the United Synagogue and Rabbinical Assembly must reassess their historically rigid positions on church-state issues, especially regarding tax assistance for parochial schools. The evidence suggests that evolving community needs require moving beyond simple separationist approaches toward more nuanced solutions that balance practical realities with core religious values and institutional integrity.