The current study was part of a large project focusing on bilingual development in the preschool classroom context. Its aim was to theorize free play as a social and language learning activity that provides opportunities for young learners to move towards second language production. The role of free play for language development in general, and its unique contribution to L2 learning inspired our work. We applied a qualitative approach to perform close observations of eight children, four L1 Arabic-speakers and four L1 Hebrew-speakers and provided numerical data about the frequency of L2 use. The analysis revealed that free play created a fruitful language-conducive context for daring to use L2 (even with mistakes), peer language mediation, creative repetition, self-talk, focus on language form, and corrective feedback for others' incorrect usage. Theorization of the role of free play in L2 production is followed by some suggestions for field applications in preschool classrooms, engaging children coming from diverse linguistic backgrounds.