The transition to primary school is widely seen as a period of multifaceted transformations and adoptions of different strategies for parents, yet relatively little is known about the lived transition experiences of parents from diverse (linguistic, cultural, socio-economic) backgrounds. This article explores the issue by examining maternal narratives in the context of having a child starting school in settings defined by family diversity through the lens of Paulo Freire's "Pedagogy of the Oppressed." Four rounds of semi-structured interviews were conducted with two mothers of children from diverse backgrounds during their first year of primary school in two neighborhoods in Reykjavík, Iceland. The findings show that, for these mothers, engagement with the Icelandic ECEC system before and during the transition to school triggered them to take action when they felt that their concerns about their child's wellbeing were not taken seriously. The mothers' experiences furthermore brought about critical re-evaluation of their cultural background.