Mother-child separations are a gendered ‘pain of imprisonment’ leaving a legacy of further trauma for mothers on release, particularly those who are not reunited with their children. Building on Haney’s contextual approach, this chapter will present a co-produced qualitative analysis of research findings on separated mothers in prison. This collaboration between a mother with lived experience of the prison system and a prison researcher will draw on feminist criminological work reflecting on personal experience of the prison system. Interweaving lived experience reflections with a study of maternal imprisonment, we discuss how imprisoned mothers’ experiences of separation from their children are mediated by social support and wider systemic issues with the criminal justice system. Three aspects were emphasised by mothers and prison staff: 1) the impact of family relationships; 2) wider systems and agencies beyond prison; 3) prison mother-baby units. We propose that a contextual understanding of mothers’ experiences is needed to work towards mitigating the harms of mother-child separation.