Conservative Jewish educators face a stark dilemma: how can they teach halakhah as binding religious law while honoring modern values of individual autonomy and moral reasoning? The tension between these competing imperatives shapes educational approaches across the Conservative movement, most notably in Israel's TALI school system. Through comparative analysis of educational philosophies - from Durkheim's emphasis on moral socialization through authority to Values Clarification methods centered on individual choice - alongside case studies of Conservative Jewish institutions, this research reveals the limitations of both authoritarian and purely choice-based pedagogies. Authoritarian approaches clash with democratic values, while choice-based methods often fail to effectively transmit traditional Jewish practices. The TALI schools' experience demonstrates that even carefully balanced approaches tend to result in students moving away from traditional observance rather than toward it. Analysis suggests that successful Conservative Jewish education fundamentally requires authentic communities that model the values being taught, as schools alone cannot substitute for genuine social environments where traditional Judaism is practiced. Without vibrant communities demonstrating meaningful Jewish life, educational institutions face severe constraints in promoting normative traditional Judaism, regardless of their pedagogical approach.