This study examined how adolescents raised solely by grandparents navigated their relationships with their parents and grandparents and how these relationships were influenced by the caregiving context. Forty-one adolescents participated in qualitative, semistructured interviews. Findings suggest that relationships with parents were primarily companionate or marked by distance and distrust. Grandchildren had strong emotional bonds to their grandparents, although they also negotiated several sources of stress. Participants also reported feelings of gratitude because of the positive influence their grandparents had on their lives. Caregiving context shaped grandchildren’s interdependence with their parents and grandparents in numerous ways. Findings highlight the complexity of grandchildren’s family relationships and underscore the value of a systemic approach to understanding youth who are being raised by grandparents.