This paper examines dilemmatic aspects of language policies in a preschool group in which three languages (Swedish, Romani and Arabic) are daily spoken. The paper points out the interaction between policy decisions on the societal level, the teachers’ interpretations of these policies, and language practices on the micro level. The preschool group is considered as a complex context for negotiating language policies and expectations concerning language use. The theoretical framework draws from Billig’s work on ideological and everyday dilemmas that are asserted to be detectable at both levels of the assay. The analysis of the ethnographic material displays that the explicit language policy formulated in the Swedish preschool curriculum leads, in practice, to ideological, pedagogical and everyday dilemmas. Moreover, an obstinacy to set rules for children’s language choice combined with the central position of free play in Swedish preschool practice has led to a situation in which children fall short of their potential to evolve bilingual competence.