Previous research has shown that differences in the speech that children are exposed to can lead to differences in their language, literacy and cognitive development, and may even affect subsequent success at school. Informed by Vygotsky’s sociocultural theory of language learning in early childhood and Sigel’s Psychological Distancing Model, this ethnographic multiple-case study analyzes maternal interaction strategies in four Chinese families in Singapore — two local and two immigrant families — to explore factors that influence choice of interaction strategies. Cross-case comparisons are made in terms of the mothers’ professional and cultural backgrounds, and within-case comparisons are made along the lines of contextual factors. The comparisons reveal both important similarities and differences in the mothers’ use of interaction strategies which was shaped by an array of social, cultural, and contextual factors.