This study explores how racialized migrant youth navigate Ontario’s child welfare, criminal justice, and immigration systems. Insights from youth, academics, practitioners, lawyers, policymakers, and social workers were gathered from a conference and contextualized using the Intersectional Life Course Theory and a critical phenomenological framework. Our analysis focuses on timing, locally and globally linked lives, social identities, and resilience, and emphasizes the interconnectedness of individual experiences within societal structures. We review systemic challenges and ethical dilemmas for young migrants, particularly concerns about fairness in potential inadmissibility or deportation consequences. We propose systemic support measures to foster resilience and disrupt adverse trajectories in order to mitigate discriminatory practices and provide targeted support for youth within these systems.