Within Orthodox Jewish early childhood programs, gender roles of the Shabbat Party promote heteronormative gender expectations that contend with values about children, teaching, and Judaism. Interviews with 15 educators suggested tensions between gender flexible attitudes and beliefs that gender unfolds naturally. Pretend play was considered a safe space for challenging gender, regulated by perceived sociocultural and religious boundaries. Conversely, the Shabbat Party roles were rigidly instituted without much examination of their implications for gender and Jewish identity development. While a few dissenting voices revealed an emerging gender consciousness, the ongoing need for dialogue, reflection, and gender flexible practices are recommended.