The cultural context of child upbringing and rights in Zimbabwe is a complex terrain shaped by a rich cultural heritage and colonial and post-colonial influences. The country has made significant progress in developing policies and laws to protect children’s rights; however, cultural practices and beliefs continue to play a substantial role in shaping childhood experiences. This chapter examines the cultural dilemmas surrounding child upbringing and rights in Zimbabwe, drawing on a desk-based and discourse analysis of existing literature and policies. The analysis reveals that cultural practices and beliefs can both support and undermine children’s rights, and that tensions exist between traditional and modern approaches to child-rearing. The main finding of this chapter is that cultural sensitivity and contextual understanding are essential in promoting children’s rights and well-being in Zimbabwe. Based on this finding, we recommend that policymakers and practitioners engage with local communities and cultural leaders to develop culturally responsive policies and programs that promote children’s rights and well-being. This requires a nuanced understanding of the cultural context and a commitment to working with local communities to develop solutions that are grounded in their experiences and values.