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This comparative study investigated the experiences of starting childcare of three immigrant children in three different learning environments in New Zealand. The notion of learning environment was explored as a way of thinking about how different people, places, and approaches to learning have interacted to create a particular site for the children’s beginning experiences in early childhood settings. The study sheds light on multiple perceptions and experiences with regard to immigrant children and their learning. Child observations, child interviews, and teacher and parent interviews were conducted in each child’s setting. Findings suggest that early childhood environments played a critical role in supporting immigrant children’s transition from homes to early childhood centres if they were informed by the principles of familiarity, care, and collaboration. Immigrant children’s motivation to drive their own learning also provoked reflection on education both in New Zealand and other immigrant-receiving countries such as Canada, the United States, and Australia.