This study used an exploratory qualitative design to examine the experiences of Afro-Caribbean service users – specifically mothers and youth – and workers of the child welfare system in Toronto, Canada. Service users and child welfare workers were purposively selected because they were of Afro-Caribbean descent and had experience in the child welfare system in Toronto. The sample consisted of nine participants, including three youth (age 18 to 25), three mothers, and three workers. Data were collected from participants through in-depth, semi-structured individual interviews, and were analyzed using open coding and comparative analysis. Mothers reported feeling that they received differential treatment by child welfare workers and other professionals with whom they interacted, and they also felt criminalized for issues that were structural in nature. Youth reported feeling angry and resentful toward the child welfare system for having been removed from their families, as they felt that this separation caused them to lose their culture, feelings of belonging, and their siblings. Workers noted that the child welfare system conflates structural barriers with personal failings, and that the system fails in understanding Afro-Caribbean culture and immigration patterns. Although the findings are not representative of the views of all Afro-Caribbean service users and workers of the child welfare system in Toronto, the narratives advance our understanding of the complex dynamics and challenges of the child welfare system.